Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. He...
Saved in:
| Published in | Nature communications Vol. 9; no. 1; pp. 611 - 10 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
09.02.2018
Nature Publishing Group Nature Portfolio |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC:
N
-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C–C bond formation occurs, providing axially chiral α-pyrone−aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations.
Axially chiral compounds are commonly found in nature. Here, the authors show the highly enantioselective construction of axially chiral biaryls via an
N
-heterocyclic carbenes-catalyzed [3+3] atroposelective annulation of ynals with cyclic 1,3-diones. |
|---|---|
| AbstractList | Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC:
N
-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C–C bond formation occurs, providing axially chiral α-pyrone−aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations.
Axially chiral compounds are commonly found in nature. Here, the authors show the highly enantioselective construction of axially chiral biaryls via an
N
-heterocyclic carbenes-catalyzed [3+3] atroposelective annulation of ynals with cyclic 1,3-diones. Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C–C bond formation occurs, providing axially chiral α-pyrone−aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations. Axially chiral compounds are commonly found in nature. Here, the authors show the highly enantioselective construction of axially chiral biaryls via an N-heterocyclic carbenes-catalyzed [3+3] atroposelective annulation of ynals with cyclic 1,3-diones. Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N -heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C–C bond formation occurs, providing axially chiral α-pyrone−aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations. Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C-C bond formation occurs, providing axially chiral α-pyrone-aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations. |
| ArticleNumber | 611 |
| Author | Guo, Donghui Wang, Jian Li, Fangyi Huang, Kuo-Wei Zhao, Changgui Munkerup, Kristin |
| Author_xml | – sequence: 1 givenname: Changgui surname: Zhao fullname: Zhao, Changgui organization: School of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing – sequence: 2 givenname: Donghui surname: Guo fullname: Guo, Donghui organization: School of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing – sequence: 3 givenname: Kristin orcidid: 0000-0001-7097-8133 surname: Munkerup fullname: Munkerup, Kristin organization: Division of Chemical and Life Sciences & Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology – sequence: 4 givenname: Kuo-Wei orcidid: 0000-0003-1900-2658 surname: Huang fullname: Huang, Kuo-Wei organization: Division of Chemical and Life Sciences & Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology – sequence: 5 givenname: Fangyi surname: Li fullname: Li, Fangyi organization: School of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing – sequence: 6 givenname: Jian orcidid: 0000-0003-1884-4546 surname: Wang fullname: Wang, Jian email: wangjian2012@tsinghua.edu.cn organization: School of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29426851$$D View this record in MEDLINE/PubMed |
| BookMark | eNp9kk1v1DAQhi1UREvpH-CAInGsAv6K7VyQUFVKpQouwAUha2JPtlml9mJnKy2_vt5NC1sO9cXWzDvPeOz3JTkIMSAhrxl9x6gw77NkUumaMlNT3ja8Fs_IEaeS1UxzcbB3PiQnOS9pWaJlRsoX5JC3kivTsCPy4zxAmIaYcUQ3DbdY_RSn4lcFU4qrvSiEsB6hCEPlYIJx8wd91W2qL_U1Tpii27hxcCWXOgyYX5HnPYwZT-73Y_L90_m3s8_11deLy7OPV7VrtJhqoEK7vlFlIECJnvWub5EpaPsOQII24DU4xj2g7kBzpTuvtFTKc2dMK47J5cz1EZZ2lYYbSBsbYbC7QEwLC2ka3IjWgQNlWspVZ2TBdtB7JV2LXve-8aKwPsys1bq7Qe8wTAnGR9DHmTBc20W8tY2hWkpaAG_vASn-XmOe7DKuUyjzW759fsYavm3zZr_NX_7DnxSBmQUuxZwT9tYN0-7pS9dhtIzarQPs7ABbHGB3DrBbNv-v9IH-ZJGYi3IRhwWmf9d-ouoOrbfFkw |
| CitedBy_id | crossref_primary_10_1039_D4QO00515E crossref_primary_10_1038_s41467_024_44743_z crossref_primary_10_1002_anie_202316739 crossref_primary_10_1021_acs_orglett_2c03642 crossref_primary_10_3390_catal8110549 crossref_primary_10_1021_jacsau_3c00814 crossref_primary_10_1021_acscatal_1c03459 crossref_primary_10_1002_anie_202212005 crossref_primary_10_1021_acs_orglett_4c00950 crossref_primary_10_1039_D1RA06155K crossref_primary_10_1039_D0QO00963F crossref_primary_10_1021_acs_joc_4c01616 crossref_primary_10_1002_ange_202502381 crossref_primary_10_1021_acs_joc_3c01194 crossref_primary_10_1039_D2OB01859D crossref_primary_10_1055_a_1694_4695 crossref_primary_10_1002_ajoc_202300371 crossref_primary_10_3390_molecules27227990 crossref_primary_10_1002_ejoc_202200243 crossref_primary_10_1038_s41467_022_31760_z crossref_primary_10_1021_acs_orglett_0c02668 crossref_primary_10_1002_cjoc_202300728 crossref_primary_10_1021_acs_orglett_8b01799 crossref_primary_10_1039_D2OB00379A crossref_primary_10_1038_s41467_019_10878_7 crossref_primary_10_1002_tcr_202300046 crossref_primary_10_1039_D0QO01339K crossref_primary_10_1002_ange_202211977 crossref_primary_10_1002_anie_202103415 crossref_primary_10_1002_ange_202117340 crossref_primary_10_1002_anie_202010606 crossref_primary_10_1039_D1QO01127H crossref_primary_10_1002_anie_201910049 crossref_primary_10_1007_s11426_023_1909_5 crossref_primary_10_1021_acs_joc_0c00657 crossref_primary_10_1021_jacs_8b06014 crossref_primary_10_1002_anie_202412805 crossref_primary_10_1002_anie_201812654 crossref_primary_10_1021_acs_orglett_9b03188 crossref_primary_10_1055_s_0042_1752718 crossref_primary_10_1021_acscatal_3c01709 crossref_primary_10_1039_D4CC06625A crossref_primary_10_1016_j_gresc_2021_03_003 crossref_primary_10_1002_chem_201903144 crossref_primary_10_1021_acs_orglett_2c00845 crossref_primary_10_3390_molecules28114306 crossref_primary_10_1002_ange_201812654 crossref_primary_10_3390_ma13163574 crossref_primary_10_1002_tcr_202400165 crossref_primary_10_1021_acs_orglett_9b01796 crossref_primary_10_1007_s11426_022_1327_4 crossref_primary_10_1038_s42004_021_00580_5 crossref_primary_10_1002_adsc_202201175 crossref_primary_10_1002_ange_202212005 crossref_primary_10_3390_catal9100863 crossref_primary_10_1039_D4SC05482B crossref_primary_10_1016_j_tet_2021_132456 crossref_primary_10_1039_D4CS01179A crossref_primary_10_1021_acs_orglett_3c04189 crossref_primary_10_1002_ange_202412805 crossref_primary_10_1039_D3GC02073H crossref_primary_10_1039_C8CC02023J crossref_primary_10_1002_ange_202100363 crossref_primary_10_1021_acs_joc_2c02392 crossref_primary_10_1039_D4GC03113J crossref_primary_10_1002_anie_202117340 crossref_primary_10_1002_ange_201910049 crossref_primary_10_1002_ange_202010606 crossref_primary_10_1016_j_tchem_2022_100017 crossref_primary_10_1039_C9QO00468H crossref_primary_10_1002_anie_202108630 crossref_primary_10_1021_acs_orglett_9b04203 crossref_primary_10_1021_acs_orglett_1c03220 crossref_primary_10_1002_anie_201903589 crossref_primary_10_1021_acs_joc_4c00330 crossref_primary_10_1038_s41467_019_11688_7 crossref_primary_10_1038_s41467_021_27771_x crossref_primary_10_1055_s_0040_1707327 crossref_primary_10_1021_acscatal_9b05443 crossref_primary_10_1002_ange_201903589 crossref_primary_10_1002_ange_202108630 crossref_primary_10_1021_acs_orglett_8b03892 crossref_primary_10_1021_acs_orglett_9b01731 crossref_primary_10_1002_ange_202311709 crossref_primary_10_1002_anie_202502381 crossref_primary_10_1002_ajoc_202200578 crossref_primary_10_1039_D1QO01672E crossref_primary_10_1002_ajoc_201900693 crossref_primary_10_1021_acscatal_4c00513 crossref_primary_10_1021_acs_joc_4c02644 crossref_primary_10_1002_ajoc_202100252 crossref_primary_10_1021_acs_joc_1c01230 crossref_primary_10_1002_chem_201803254 crossref_primary_10_1002_chem_202102797 crossref_primary_10_1039_C9CC06360A crossref_primary_10_1002_anie_202311709 crossref_primary_10_1002_ange_202103415 crossref_primary_10_1002_anie_202211977 crossref_primary_10_1002_anie_202404979 crossref_primary_10_1002_ange_201914049 crossref_primary_10_1021_acs_joc_9b00320 crossref_primary_10_1021_acs_orglett_1c01221 crossref_primary_10_1021_acs_joc_9b00161 crossref_primary_10_1002_ange_202316739 crossref_primary_10_1038_s41467_024_46376_8 crossref_primary_10_1021_acs_orglett_9b03014 crossref_primary_10_1021_acscatal_2c05570 crossref_primary_10_1039_D0CC04661B crossref_primary_10_1002_chem_202402843 crossref_primary_10_1021_jacs_1c04759 crossref_primary_10_1039_D3SC06444A crossref_primary_10_1021_acs_chemrev_0c01306 crossref_primary_10_1002_anie_202100363 crossref_primary_10_1002_adsc_201800857 crossref_primary_10_1039_D4RA05596A crossref_primary_10_1002_ange_202404979 crossref_primary_10_3390_molecules28073142 crossref_primary_10_1021_acs_orglett_1c01191 crossref_primary_10_1002_anie_201914049 |
| Cites_doi | 10.1021/cr100155e 10.1021/ar00178a005 10.1038/ncomms15238 10.1021/ja00316a063 10.1002/anie.200900469 10.1002/anie.201402441 10.1002/anie.201304039 10.1038/nature13384 10.1021/ja027411v 10.1002/anie.201406684 10.1021/ja0319442 10.1021/ja0201505 10.1002/anie.200454164 10.1021/ol202272t 10.1002/anie.201303247 10.1002/anie.200462661 10.1002/anie.201508419 10.1021/ja905501z 10.1021/cs300020t 10.1021/ja108717r 10.1039/c2cs15333e 10.1002/anie.201308237 10.1021/jacs.6b03609 10.1039/b821092f 10.1002/cmdc.201000485 10.1021/ja401709k 10.1021/ja910540j 10.1002/anie.199009771 10.1038/nchem.727 10.1021/jacs.5b10152 10.1002/anie.201204145 10.1021/ol062940f 10.1039/C1SC00397F 10.1039/C5CS00012B 10.1248/yakushi1881.63.6_296 10.1002/anie.201103792 10.1007/128_2008_18 10.1002/anie.201004593 10.1021/ja048131d 10.1021/jo050645n 10.1021/acs.chemrev.5b00060 10.1039/C4SC03726J 10.1002/anie.200503042 10.1246/cl.2008.2 10.1021/ja990646v 10.1021/ja910666n 10.1002/anie.199418421 10.1021/ja01547a064 10.1021/ja111067j 10.1021/ja103631u 10.1021/ar030050j 10.1021/ol052826h 10.1021/ar400239v 10.1038/ncomms10677 10.1039/c3cs35522e 10.1021/ja005622z 10.1021/ja104297g 10.1021/ja211069f 10.1021/ja062707c 10.1021/ja409669r 10.1021/ja00232a030 |
| ContentType | Journal Article |
| Copyright | The Author(s) 2018 2018. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. |
| Copyright_xml | – notice: The Author(s) 2018 – notice: 2018. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. |
| DBID | C6C AAYXX CITATION NPM 3V. 7QL 7QP 7QR 7SN 7SS 7ST 7T5 7T7 7TM 7TO 7X7 7XB 88E 8AO 8FD 8FE 8FG 8FH 8FI 8FJ 8FK ABUWG AEUYN AFKRA ARAPS AZQEC BBNVY BENPR BGLVJ BHPHI C1K CCPQU DWQXO FR3 FYUFA GHDGH GNUQQ H94 HCIFZ K9. LK8 M0S M1P M7P P5Z P62 P64 PHGZM PHGZT PIMPY PJZUB PKEHL PPXIY PQEST PQGLB PQQKQ PQUKI PRINS RC3 SOI 5PM DOA |
| DOI | 10.1038/s41467-018-02952-3 |
| DatabaseName | Springer Nature OA Free Journals CrossRef PubMed ProQuest Central (Corporate) Bacteriology Abstracts (Microbiology B) Calcium & Calcified Tissue Abstracts Chemoreception Abstracts Ecology Abstracts Entomology Abstracts (Full archive) Environment Abstracts Immunology Abstracts Industrial and Applied Microbiology Abstracts (Microbiology A) Nucleic Acids Abstracts Oncogenes and Growth Factors Abstracts Health & Medical Collection ProQuest Central (purchase pre-March 2016) Medical Database (Alumni Edition) ProQuest Pharma Collection Technology Research Database ProQuest SciTech Collection ProQuest Technology Collection ProQuest Natural Science Collection Hospital Premium Collection Hospital Premium Collection (Alumni Edition) ProQuest Central (Alumni) (purchase pre-March 2016) ProQuest Central (Alumni) ProQuest One Sustainability ProQuest Central UK/Ireland Advanced Technologies & Aerospace Collection ProQuest Central Essentials Biological Science Collection ProQuest Central Technology Collection Natural Science Collection Environmental Sciences and Pollution Management ProQuest One Community College ProQuest Central Engineering Research Database Health Research Premium Collection Health Research Premium Collection (Alumni) ProQuest Central Student AIDS and Cancer Research Abstracts SciTech Premium Collection ProQuest Health & Medical Complete (Alumni) ProQuest Biological Science Collection ProQuest Health & Medical Collection Medical Database Biological Science Database Advanced Technologies & Aerospace Database ProQuest Advanced Technologies & Aerospace Collection Biotechnology and BioEngineering Abstracts ProQuest Central Premium ProQuest One Academic (New) Publicly Available Content Database ProQuest Health & Medical Research Collection ProQuest One Academic Middle East (New) ProQuest One Health & Nursing ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Applied & Life Sciences ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central China Genetics Abstracts Environment Abstracts PubMed Central (Full Participant titles) DOAJ Directory of Open Access Journals |
| DatabaseTitle | CrossRef PubMed Publicly Available Content Database ProQuest Central Student Oncogenes and Growth Factors Abstracts ProQuest Advanced Technologies & Aerospace Collection ProQuest Central Essentials Nucleic Acids Abstracts SciTech Premium Collection ProQuest Central China Environmental Sciences and Pollution Management ProQuest One Applied & Life Sciences ProQuest One Sustainability Health Research Premium Collection Natural Science Collection Health & Medical Research Collection Biological Science Collection Chemoreception Abstracts Industrial and Applied Microbiology Abstracts (Microbiology A) ProQuest Central (New) ProQuest Medical Library (Alumni) Advanced Technologies & Aerospace Collection ProQuest Biological Science Collection ProQuest One Academic Eastern Edition ProQuest Hospital Collection ProQuest Technology Collection Health Research Premium Collection (Alumni) Biological Science Database Ecology Abstracts ProQuest Hospital Collection (Alumni) Biotechnology and BioEngineering Abstracts Entomology Abstracts ProQuest Health & Medical Complete ProQuest One Academic UKI Edition Engineering Research Database ProQuest One Academic Calcium & Calcified Tissue Abstracts ProQuest One Academic (New) Technology Collection Technology Research Database ProQuest One Academic Middle East (New) ProQuest Health & Medical Complete (Alumni) ProQuest Central (Alumni Edition) ProQuest One Community College ProQuest One Health & Nursing ProQuest Natural Science Collection ProQuest Pharma Collection ProQuest Central ProQuest Health & Medical Research Collection Genetics Abstracts Health and Medicine Complete (Alumni Edition) ProQuest Central Korea Bacteriology Abstracts (Microbiology B) AIDS and Cancer Research Abstracts ProQuest SciTech Collection Advanced Technologies & Aerospace Database ProQuest Medical Library Immunology Abstracts Environment Abstracts ProQuest Central (Alumni) |
| DatabaseTitleList | Publicly Available Content Database CrossRef PubMed |
| Database_xml | – sequence: 1 dbid: C6C name: Springer Nature OA Free Journals url: http://www.springeropen.com/ sourceTypes: Publisher – sequence: 2 dbid: DOA name: DOAJ Directory of Open Access Journals url: https://www.doaj.org/ sourceTypes: Open Website – sequence: 3 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 4 dbid: 8FG name: ProQuest Technology Collection url: https://search.proquest.com/technologycollection1 sourceTypes: Aggregation Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Biology |
| EISSN | 2041-1723 |
| EndPage | 10 |
| ExternalDocumentID | oai_doaj_org_article_caca689026b84ad7bafd64c9ed7fd5d3 PMC5807440 29426851 10_1038_s41467_018_02952_3 |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GroupedDBID | --- 0R~ 39C 3V. 53G 5VS 70F 7X7 88E 8AO 8FE 8FG 8FH 8FI 8FJ AAHBH AAJSJ ABUWG ACGFO ACGFS ACIWK ACMJI ACPRK ACSMW ADBBV ADFRT ADMLS ADRAZ AENEX AEUYN AFKRA AFRAH AHMBA AJTQC ALIPV ALMA_UNASSIGNED_HOLDINGS AMTXH AOIJS ARAPS ASPBG AVWKF AZFZN BAPOH BBNVY BCNDV BENPR BGLVJ BHPHI BPHCQ BVXVI C6C CCPQU DIK EBLON EBS EE. EMOBN F5P FEDTE FYUFA GROUPED_DOAJ HCIFZ HMCUK HVGLF HYE HZ~ KQ8 LK8 M1P M48 M7P M~E NAO O9- OK1 P2P P62 PIMPY PQQKQ PROAC PSQYO RNS RNT RNTTT RPM SNYQT SV3 TSG UKHRP AASML AAYXX CITATION PHGZM PHGZT NPM 7QL 7QP 7QR 7SN 7SS 7ST 7T5 7T7 7TM 7TO 7XB 8FD 8FK AARCD AZQEC C1K DWQXO FR3 GNUQQ H94 K9. P64 PJZUB PKEHL PPXIY PQEST PQGLB PQUKI PRINS RC3 SOI 5PM PUEGO |
| ID | FETCH-LOGICAL-c573t-a037cf56038ae4ed1fcf9e16a9fbaa4a78ad7ac12dae7ba7267bd67466d2c8893 |
| IEDL.DBID | M48 |
| ISSN | 2041-1723 |
| IngestDate | Wed Aug 27 01:25:44 EDT 2025 Thu Aug 21 14:07:25 EDT 2025 Wed Aug 13 04:05:13 EDT 2025 Mon Jul 21 05:55:25 EDT 2025 Tue Jul 01 02:21:09 EDT 2025 Thu Apr 24 22:50:22 EDT 2025 Fri Feb 21 02:39:57 EST 2025 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 1 |
| Language | English |
| License | Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c573t-a037cf56038ae4ed1fcf9e16a9fbaa4a78ad7ac12dae7ba7267bd67466d2c8893 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
| ORCID | 0000-0003-1900-2658 0000-0003-1884-4546 0000-0001-7097-8133 |
| OpenAccessLink | http://journals.scholarsportal.info/openUrl.xqy?doi=10.1038/s41467-018-02952-3 |
| PMID | 29426851 |
| PQID | 2000011523 |
| PQPubID | 546298 |
| PageCount | 10 |
| ParticipantIDs | doaj_primary_oai_doaj_org_article_caca689026b84ad7bafd64c9ed7fd5d3 pubmedcentral_primary_oai_pubmedcentral_nih_gov_5807440 proquest_journals_2000011523 pubmed_primary_29426851 crossref_citationtrail_10_1038_s41467_018_02952_3 crossref_primary_10_1038_s41467_018_02952_3 springer_journals_10_1038_s41467_018_02952_3 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2018-02-09 |
| PublicationDateYYYYMMDD | 2018-02-09 |
| PublicationDate_xml | – month: 02 year: 2018 text: 2018-02-09 day: 09 |
| PublicationDecade | 2010 |
| PublicationPlace | London |
| PublicationPlace_xml | – name: London – name: England |
| PublicationTitle | Nature communications |
| PublicationTitleAbbrev | Nat Commun |
| PublicationTitleAlternate | Nat Commun |
| PublicationYear | 2018 |
| Publisher | Nature Publishing Group UK Nature Publishing Group Nature Portfolio |
| Publisher_xml | – name: Nature Publishing Group UK – name: Nature Publishing Group – name: Nature Portfolio |
| References | LinkASparrCOrganocatalytic atroposelective aldol condensation: synthesis of axially chiral biaryls by arene formationAngew. Chem. Int. Ed.201453545854611:CAS:528:DC%2BC2cXmslams74%3D10.1002/anie.201402441 WannerBMahatthananchaiJBodeJWEnantioselective synthesis of dihydropyridinones via NHC-catalyzed Aza-Claisen reactionOrg. Lett.201113537853811:CAS:528:DC%2BC3MXhtFCgsLzN10.1021/ol202272t21905682 EndersDBalensieferTNucleophilic carbenes in asymmetric organocatalysisAcc. Chem. Res.2004375345411:CAS:528:DC%2BD2cXisVequ7Y%3D10.1021/ar030050j15311952 KaeobamrungJMahatthananchaiJZhengPBodeJWAn enantioselective claisen rearrangement catalyzed by N-heterocyclic carbenesJ. Am. Chem. Soc.2010132881088121:CAS:528:DC%2BC3cXnsFGmtLw%3D10.1021/ja103631u205501272902991 NoyoriRTakayaHBINAP: an efficient chiral element for asymmetric catalysisAcc. Chem. Res.1990233453501:CAS:528:DyaK3cXlsFWmsrw%3D10.1021/ar00178a005 Bringmann, G., Walter, R. & Weirich, R. in Methods of Organic Chemistry (Houben Weyl) 4th edn, Vol. E21a (eds Helmchen, G., Hoffmann, R. W., Mulzer, J. & Schaumann, E.) 567 (Thieme, Stuttgart, Germany, 1995). YuCHuangHZhangYWangWDynamic kinetic resolution of biaryl lactones via a chiral bifunctional amine thiourea-catalyzed highly atropo-enantioselective transesterificationJ. Am. Chem. Soc.2016138695669581:CAS:528:DC%2BC28XosFSmtLg%3D10.1021/jacs.6b0360927218264 ChenYHAtroposelective synthesis of axially chiral biaryldiols via organocatalytic arylation of 2-naphtholsJ. Am. Chem. Soc.201513715062150651:CAS:528:DC%2BC2MXhvVWnsbjJ10.1021/jacs.5b1015226560999 BreslowROn the mechanism of thiamine action. IV.1 Evidence from studies on model systemsJ. Am. Chem. Soc.195880371937261:CAS:528:DyaG1MXhslGqsA%3D%3D10.1021/ja01547a064 UozumiYMatsuuraYArakawaTYamadaYMAAsymmetric Suzuki–Miyaura coupling in water with a chiral palladium catalyst supported on an amphiphilic resinAngew. Chem. Int. Ed.200948270827101:CAS:528:DC%2BD1MXks1Clu7Y%3D10.1002/anie.200900469 LaPlanteSREdwardsPJFaderLDKakalianAHuckeORevealing atropisomer axial chirality in drug discoveryChemMedChem201165055131:CAS:528:DC%2BC3MXisFCjs7w%3D10.1002/cmdc.20100048521360821 BugautXGloriusFN-heterocyclic carbenes and beyondChem. Soc. Rev.201241351135221:CAS:528:DC%2BC38Xlt1yntr0%3D10.1039/c2cs15333e22377957 De SarkarSGrimmeSStuderANHC catalyzed oxidations of aldehydes to esters: chemoselective acylation of alcohols in presence of aminesJ. Am. Chem. Soc.20101321190119110.1021/ja910540j20055393 YinJBuchwaldSLA catalytic asymmetric suzuki coupling for the synthesis of axially chiral biaryl compoundsJ. Am. Chem. Soc.200012212051120521:CAS:528:DC%2BD3cXnvFarsLY%3D10.1021/ja005622z HayashiTHayashizakiKKiyoiTItoYAsymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition-metal complexes. 6. Practical asymmetric synthesis of 1,1’-binaphthyls via asymmetric cross-coupling with a chiral [(alkoxyalkyl)ferrocenyl]monophosphine/nickel catalystJ. Am. Chem. Soc.1988110815381561:CAS:528:DyaL1MXhtFCnsL0%3D10.1021/ja00232a030 Bringmann, G., Gìnther, C., Ochse, M., Schupp, O. & Tasler, S. in Progress in the Chemistry of Organic Natural Products, Vol. 82 (eds. Herz, W., Falk, H., Kirby, G. W., Moore, R. E.) 1–129 (Springer, Berlin, 1998). Nishii, Y., Wakasugi, K., Koga, K. & Tanabe, Y. Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral α-arylnaphthalenes. J. Am. Chem. Soc. 126, 5358–5359 (2004). MooreJLRovisTCarbene catalystsTop. Curr. Chem.20092917714410.1007/128_2008_18 LiGQOrganocatalytic aryl–aryl bond formation: an atroposelective [3,3]-rearrangement approach to BINAM derivativesJ. Am. Chem. Soc.2013135741474171:CAS:528:DC%2BC3sXntVWrs7g%3D10.1021/ja401709k23659490 MaGDengJSibiMPFluxionally chiral DMAP catalysts: kinetic resolution of axially chiral biaryl compoundsAngew. Chem. Int. Ed.20145311818118211:CAS:528:DC%2BC2cXhtlOmurrI10.1002/anie.201406684 BringmannGAtroposelective synthesis of axially chiral biaryl compoundsAngew. Chem. Int. Ed.200544538454271:CAS:528:DC%2BD2MXpvF2ks7c%3D10.1002/anie.200462661 HopkinsonMNRichterCSchedlerMGloriusFAn overview of N-heterocyclic carbenesNature20145104854962014Natur.510..485H1:CAS:528:DC%2BC2cXhtVCqu7fO10.1038/nature1338424965649 ZhangJ-WDiscovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reactionNat. Commun.20167106772016NatCo...710677Z10.1038/ncomms10677268645104753251 ShenXJonesGOWatsonDABhayanaBBuchwaldSLEnantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki−Miyaura reaction: substrate scope and quantum mechanical investigationsJ. Am. Chem. Soc.201013211278112871:CAS:528:DC%2BC3cXptFOls7c%3D10.1021/ja104297g206986952924746 KravinaAGMahatthananchaiJBodeJWEnantioselective, NHC-catalyzed annulations of trisubstituted enals and cyclic N-sulfonylimines via α,ß-unsaturated acyl azoliumsAngew. Chem. Int. Ed.201251943394361:CAS:528:DC%2BC38Xht1aqtb%2FN10.1002/anie.201204145 Kerr, M. S., Read de Alaniz, J. & Rovis, J. Highly enantioselective catalytic intramolecular Stetter reaction. J. Am. Chem. Soc.124, 10298–10299 (2002). Frisch, M. J. et al. Gaussian 09 Revision D.09 (Gaussian Inc., Wallingford, 2016). ShirakawaSWuXMaruokaKCatalytic asymmetric synthesis of axially chiral O-Iodoanilides by phase-transfer catalyzed alkylationsJ. Am. Chem. Soc.20121349169191:CAS:528:DC%2BC3MXhs1OjurvO10.1021/ja211069f22208662 RyanSJCandishLLuptonDWAcyl anion free n-heterocyclic carbene organocatalysisChem. Soc. Rev.201342490649171:CAS:528:DC%2BC3sXot1ersrg%3D10.1039/c3cs35522e23403488 KozlowskiMCMorganBJLintonECTotal synthesis of chiral biaryl natural products by asymmetric biaryl couplingChem. Soc. Rev.200938319332071:CAS:528:DC%2BD1MXht12ht7rM10.1039/b821092f198473512904069 SaitoSKanoTMutoHNakadaiHYamamotoHAsymmetric coupling of phenols with arylleadsJ. Am. Chem. Soc.1999121894389441:CAS:528:DyaK1MXlslChsbg%3D10.1021/ja990646v PhillipsEMChanAScheidtKADiscovering new reactions with N-heterocyclic carbene catalysisAldrichimica Acta20094255661:CAS:528:DC%2BC3cXktVSgsb8%3D210721302975109 XuGFuWLiuGSenanayakeCHTangWEfficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactionsJ. Am. Chem. Soc.20141365705731:CAS:528:DC%2BC3sXhs1KktLjE10.1021/ja409669r24147559 ShibataTFujimotoTYokotaKTakagiKIridium complex-catalyzed highly enantio- and diastereoselective [2+2+2] cycloaddition for the synthesis of axially chiral teraryl compoundsJ. Am. Chem. Soc.2004126838283831:CAS:528:DC%2BD2cXkvFyit7g%3D10.1021/ja048131d15237987 GaoHPractical organocatalytic synthesis of functionalized non-C2-symmetrical atropisomeric biarylsAngew. Chem. Int. Ed.2016555665711:CAS:528:DC%2BC2MXhvVOlt7rK10.1002/anie.201508419 BringmannGWalterRWeirichRThe directed synthesis of biaryl compounds: modern concepts and strategiesAngew. Chem. Int. Ed.19902997799110.1002/anie.199009771 BrandesSBellaMKjarsgaardAJøgensenKAChirally aminated 2-naphthols—organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel–Crafts aminationAngew. Chem. Int. Ed.200645114711511:CAS:528:DC%2BD28XhslaqtL0%3D10.1002/anie.200503042 YamamotoTAkaiYNagataYSuginomeMHighly enantioselective synthesis of axially chiral biarylphosphonates: asymmetric Suzuki–Miyaura coupling using high-molecular-weight, helically chiral polyquinoxaline-based phosphinesAngew. Chem. Int. Ed.201150884488471:CAS:528:DC%2BC3MXpvVantrc%3D10.1002/anie.201103792 LipshutzBHKayserFLiuZPAsymmetric synthesis of biaryls by intramolecular oxidative couplings of cyanocuprate intermediatesAngew. Chem. Int. Ed.1994331842184410.1002/anie.199418421 MakiBEChanAPhillipsEMScheidtKATandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenesOrg. Lett.200793713741:CAS:528:DC%2BD28Xhtlaks7%2FP10.1021/ol062940f17217307 RyanSJCandishLLuptonDWN-heterocyclic carbene-catalyzed generation of α,ß-unsaturated acyl imidazoliums: synthesis of dihydropyranones by their reaction with enolatesJ. Am. Chem. Soc.200913114176141771:CAS:528:DC%2BD1MXhtFCjtrvE10.1021/ja905501z19757788 GutnovACobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: synthesis of enantiomerically enriched atropoisomers of 2-arylpyridinesAngew. Chem. Int. Ed.200443379537971:CAS:528:DC%2BD2cXmt12rtro%3D10.1002/anie.200454164 MeyersAWettlauferDThe complete intramolecular transfer of a central chiral element to an axial chiral element. Oxid. (S)-4-naphthyldihydroquinolines to (S)-4-naphthylquinolines J. Am. Chem. Soc.1984106113511361:CAS:528:DyaL2cXosFGksg%3D%3D10.1021/ja00316a063 Kerr, M. S., Read de Alaniz, J. & Rovis, T. Efficient synthesis of achiral and chiral 1,2,4-triazolium salts: bench stable precursors for N-heterocyclic carbenes. J. Org. Chem.70, 5725–5728 (2005). BringmannGGulderTGulderTAMBreuningMAtroposelective total synthesis of axially chiral biaryl natural productsChem. Rev.20111115636391:CAS:528:DC%2BC3cXht1OqtbnP10.1021/cr100155e20939606 De SarkarSStuderANHC-catalyzed Michael addition to α,ß-unsaturated aldehydes by redox activationAngew. Chem. Int. Ed.2010499266926910.1002/anie.201004593 Wencel-DelordJPanossianALerouxFRColobertFRecent advances and new concepts for the synthesis of axially stereoenriched biarylsChem. Soc. Rev.201544341834301:CAS:528:DC%2BC2MXntVCisrk%3D10.1039/C5CS00012B25904287 RyanSJCandishLLuptonDWN-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with α,ß-unsaturated acid fluoridesJ. Am. Chem. Soc.2011133469446971:CAS:528:DC%2BC3MXivFyisrs%3D10.1021/ja111067j21391673 UkaiTTanakaRDokawaTA new catalyst for the acyloin condensationJ. Pharm. Soc. Jpn.1943632963041:CAS:528:DyaG3MXivFKnuw%3D%3D10.1248/yakushi1881.63.6_296 ShirakawaSLiuSMaruokaKKinetic resolution of axially chiral 2-amino-1,1′-biaryls by phase-transfer-catalyzed N-allylationAngew. Chem. Int. Ed.20135214200142031:CAS:528:DC%2BC3sXhslOlsLzN10.1002/anie.201308237 MahatthananchaiJBodeJWOn the mechanism of N-heterocyclic carbene-catalyze A Meyers (2952_CR26) 1984; 106 J Mahatthananchai (2952_CR41) 2014; 47 S De Sarkar (2952_CR53) 2010; 132 C Yu (2952_CR23) 2016; 138 S Shirakawa (2952_CR19) 2013; 52 Y Uozumi (2952_CR30) 2009; 48 M He (2952_CR60) 2006; 128 EM Phillips (2952_CR37) 2009; 42 SJ Ryan (2952_CR46) 2009; 131 X Bugaut (2952_CR39) 2012; 41 J Cheng (2952_CR54) 2013; 52 G Bringmann (2952_CR3) 2011; 111 K Zeitler (2952_CR45) 2006; 8 2952_CR8 S Shirakawa (2952_CR18) 2012; 134 2952_CR1 T Hayashi (2952_CR28) 1988; 110 T Shibata (2952_CR35) 2004; 126 R Noyori (2952_CR5) 1990; 23 CK De (2952_CR21) 2013; 52 T Yamamoto (2952_CR32) 2011; 50 GQ Li (2952_CR14) 2013; 135 J Mahatthananchai (2952_CR51) 2012; 2 G Xu (2952_CR33) 2014; 136 A Gutnov (2952_CR34) 2004; 43 AV Vorogushin (2952_CR12) 2002; 124 A Link (2952_CR15) 2014; 53 X Shen (2952_CR31) 2010; 132 J Mahatthananchai (2952_CR62) 2012; 3 B Wanner (2952_CR48) 2011; 13 G Bringmann (2952_CR6) 2005; 44 S Brandes (2952_CR17) 2006; 45 YH Chen (2952_CR16) 2015; 137 S De Sarkar (2952_CR55) 2010; 49 T Ukai (2952_CR63) 1943; 63 SJ Ryan (2952_CR47) 2011; 133 T Rovis (2952_CR61) 2008; 37 J Wencel-Delord (2952_CR7) 2015; 44 AG Kravina (2952_CR49) 2012; 51 2952_CR59 2952_CR58 R Breslow (2952_CR64) 1958; 80 H Gao (2952_CR20) 2016; 55 2952_CR11 BE Maki (2952_CR52) 2007; 9 B Cardinal-David (2952_CR56) 2010; 132 G Ma (2952_CR22) 2014; 53 SR LaPlante (2952_CR4) 2011; 6 BH Lipshutz (2952_CR10) 1994; 33 DM Flanigan (2952_CR43) 2015; 15 JL Moore (2952_CR38) 2009; 291 MC Kozlowski (2952_CR2) 2009; 38 S Saito (2952_CR29) 1999; 121 F Guo (2952_CR13) 2011; 133 D Enders (2952_CR36) 2004; 37 SJ Ryan (2952_CR40) 2013; 42 J Kaeobamrung (2952_CR50) 2010; 132 DEA Raup (2952_CR57) 2010; 2 S-C Zheng (2952_CR25) 2017; 8 G Bringmann (2952_CR9) 1990; 29 J Yin (2952_CR27) 2000; 122 MN Hopkinson (2952_CR42) 2014; 510 L Candish (2952_CR44) 2015; 6 2952_CR65 J-W Zhang (2952_CR24) 2016; 7 |
| References_xml | – reference: ZhengS-COrganocatalytic atroposelective synthesis of axially chiral styrenesNat. Commun.20178152382017NatCo...815238Z10.1038/ncomms15238284668725418600 – reference: ChengJHuangZChiYRNHC organocatalytic formal LUMO activation of α,ß-unsaturated esters for reaction with enamidesAngew. Chem. Int. Ed.201352859285961:CAS:528:DC%2BC3sXhtFShtrjN10.1002/anie.201303247 – reference: LiGQOrganocatalytic aryl–aryl bond formation: an atroposelective [3,3]-rearrangement approach to BINAM derivativesJ. Am. Chem. Soc.2013135741474171:CAS:528:DC%2BC3sXntVWrs7g%3D10.1021/ja401709k23659490 – reference: RyanSJCandishLLuptonDWN-heterocyclic carbene-catalyzed generation of α,ß-unsaturated acyl imidazoliums: synthesis of dihydropyranones by their reaction with enolatesJ. Am. Chem. Soc.200913114176141771:CAS:528:DC%2BD1MXhtFCjtrvE10.1021/ja905501z19757788 – reference: XuGFuWLiuGSenanayakeCHTangWEfficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactionsJ. Am. Chem. Soc.20141365705731:CAS:528:DC%2BC3sXhs1KktLjE10.1021/ja409669r24147559 – reference: BringmannGAtroposelective synthesis of axially chiral biaryl compoundsAngew. Chem. Int. Ed.200544538454271:CAS:528:DC%2BD2MXpvF2ks7c%3D10.1002/anie.200462661 – reference: Kerr, M. S., Read de Alaniz, J. & Rovis, J. Highly enantioselective catalytic intramolecular Stetter reaction. J. Am. Chem. Soc.124, 10298–10299 (2002). – reference: YinJBuchwaldSLA catalytic asymmetric suzuki coupling for the synthesis of axially chiral biaryl compoundsJ. Am. Chem. Soc.200012212051120521:CAS:528:DC%2BD3cXnvFarsLY%3D10.1021/ja005622z – reference: ZeitlerKStereoselective synthesis of (E)-α,ß-unsaturated esters via carbene-catalyzed redox esterificationOrg. Lett.200686376401:CAS:528:DC%2BD28XoslaisQ%3D%3D10.1021/ol052826h16468730 – reference: Nishii, Y., Wakasugi, K., Koga, K. & Tanabe, Y. Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral α-arylnaphthalenes. J. Am. Chem. Soc. 126, 5358–5359 (2004). – reference: Bringmann, G., Walter, R. & Weirich, R. in Methods of Organic Chemistry (Houben Weyl) 4th edn, Vol. E21a (eds Helmchen, G., Hoffmann, R. W., Mulzer, J. & Schaumann, E.) 567 (Thieme, Stuttgart, Germany, 1995). – reference: HayashiTHayashizakiKKiyoiTItoYAsymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition-metal complexes. 6. Practical asymmetric synthesis of 1,1’-binaphthyls via asymmetric cross-coupling with a chiral [(alkoxyalkyl)ferrocenyl]monophosphine/nickel catalystJ. Am. Chem. Soc.1988110815381561:CAS:528:DyaL1MXhtFCnsL0%3D10.1021/ja00232a030 – reference: NoyoriRTakayaHBINAP: an efficient chiral element for asymmetric catalysisAcc. Chem. Res.1990233453501:CAS:528:DyaK3cXlsFWmsrw%3D10.1021/ar00178a005 – reference: Frisch, M. J. et al. Gaussian 09 Revision D.09 (Gaussian Inc., Wallingford, 2016). – reference: RyanSJCandishLLuptonDWN-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with α,ß-unsaturated acid fluoridesJ. Am. Chem. Soc.2011133469446971:CAS:528:DC%2BC3MXivFyisrs%3D10.1021/ja111067j21391673 – reference: DeCKPesciaioliFListBCatalytic asymmetric benzidine rearrangementAngew. Chem. Int. Ed.201352929392951:CAS:528:DC%2BC3sXhtVOjt7jJ10.1002/anie.201304039 – reference: RyanSJCandishLLuptonDWAcyl anion free n-heterocyclic carbene organocatalysisChem. Soc. Rev.201342490649171:CAS:528:DC%2BC3sXot1ersrg%3D10.1039/c3cs35522e23403488 – reference: KravinaAGMahatthananchaiJBodeJWEnantioselective, NHC-catalyzed annulations of trisubstituted enals and cyclic N-sulfonylimines via α,ß-unsaturated acyl azoliumsAngew. Chem. Int. Ed.201251943394361:CAS:528:DC%2BC38Xht1aqtb%2FN10.1002/anie.201204145 – reference: HopkinsonMNRichterCSchedlerMGloriusFAn overview of N-heterocyclic carbenesNature20145104854962014Natur.510..485H1:CAS:528:DC%2BC2cXhtVCqu7fO10.1038/nature1338424965649 – reference: BringmannGGulderTGulderTAMBreuningMAtroposelective total synthesis of axially chiral biaryl natural productsChem. Rev.20111115636391:CAS:528:DC%2BC3cXht1OqtbnP10.1021/cr100155e20939606 – reference: MooreJLRovisTCarbene catalystsTop. Curr. Chem.20092917714410.1007/128_2008_18 – reference: RovisTDevelopment of chiral bicyclic triazolium salt organic catalysts: the importance of the N-aryl substituentChem. Lett.200837271:CAS:528:DC%2BD1cXhtFarsLk%3D10.1246/cl.2008.2 – reference: De SarkarSGrimmeSStuderANHC catalyzed oxidations of aldehydes to esters: chemoselective acylation of alcohols in presence of aminesJ. Am. Chem. Soc.20101321190119110.1021/ja910540j20055393 – reference: FlaniganDMRomanov-MichailidisFWhiteNARovisTOrganocatalytic reactions enabled by N‑heterocyclic carbenesChem. Rev.2015159307938710.1021/acs.chemrev.5b00060 – reference: Kerr, M. S., Read de Alaniz, J. & Rovis, T. Efficient synthesis of achiral and chiral 1,2,4-triazolium salts: bench stable precursors for N-heterocyclic carbenes. J. Org. Chem.70, 5725–5728 (2005). – reference: LipshutzBHKayserFLiuZPAsymmetric synthesis of biaryls by intramolecular oxidative couplings of cyanocuprate intermediatesAngew. Chem. Int. Ed.1994331842184410.1002/anie.199418421 – reference: GutnovACobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: synthesis of enantiomerically enriched atropoisomers of 2-arylpyridinesAngew. Chem. Int. Ed.200443379537971:CAS:528:DC%2BD2cXmt12rtro%3D10.1002/anie.200454164 – reference: UkaiTTanakaRDokawaTA new catalyst for the acyloin condensationJ. Pharm. Soc. Jpn.1943632963041:CAS:528:DyaG3MXivFKnuw%3D%3D10.1248/yakushi1881.63.6_296 – reference: ShirakawaSWuXMaruokaKCatalytic asymmetric synthesis of axially chiral O-Iodoanilides by phase-transfer catalyzed alkylationsJ. Am. Chem. Soc.20121349169191:CAS:528:DC%2BC3MXhs1OjurvO10.1021/ja211069f22208662 – reference: ShirakawaSLiuSMaruokaKKinetic resolution of axially chiral 2-amino-1,1′-biaryls by phase-transfer-catalyzed N-allylationAngew. Chem. Int. Ed.20135214200142031:CAS:528:DC%2BC3sXhslOlsLzN10.1002/anie.201308237 – reference: BugautXGloriusFN-heterocyclic carbenes and beyondChem. Soc. Rev.201241351135221:CAS:528:DC%2BC38Xlt1yntr0%3D10.1039/c2cs15333e22377957 – reference: BrandesSBellaMKjarsgaardAJøgensenKAChirally aminated 2-naphthols—organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel–Crafts aminationAngew. Chem. Int. Ed.200645114711511:CAS:528:DC%2BD28XhslaqtL0%3D10.1002/anie.200503042 – reference: LaPlanteSREdwardsPJFaderLDKakalianAHuckeORevealing atropisomer axial chirality in drug discoveryChemMedChem201165055131:CAS:528:DC%2BC3MXisFCjs7w%3D10.1002/cmdc.20100048521360821 – reference: ChenYHAtroposelective synthesis of axially chiral biaryldiols via organocatalytic arylation of 2-naphtholsJ. Am. Chem. Soc.201513715062150651:CAS:528:DC%2BC2MXhvVWnsbjJ10.1021/jacs.5b1015226560999 – reference: De SarkarSStuderANHC-catalyzed Michael addition to α,ß-unsaturated aldehydes by redox activationAngew. Chem. Int. Ed.2010499266926910.1002/anie.201004593 – reference: LinkASparrCOrganocatalytic atroposelective aldol condensation: synthesis of axially chiral biaryls by arene formationAngew. Chem. Int. Ed.201453545854611:CAS:528:DC%2BC2cXmslams74%3D10.1002/anie.201402441 – reference: BringmannGWalterRWeirichRThe directed synthesis of biaryl compounds: modern concepts and strategiesAngew. Chem. Int. Ed.19902997799110.1002/anie.199009771 – reference: ZhangJ-WDiscovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reactionNat. Commun.20167106772016NatCo...710677Z10.1038/ncomms10677268645104753251 – reference: Cardinal-DavidBRaupDEAScheidtKACooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolatesJ. Am. Chem. Soc.2010132534553471:CAS:528:DC%2BC3cXjvFKjsrs%3D10.1021/ja910666n203451862863089 – reference: SaitoSKanoTMutoHNakadaiHYamamotoHAsymmetric coupling of phenols with arylleadsJ. Am. Chem. Soc.1999121894389441:CAS:528:DyaK1MXlslChsbg%3D10.1021/ja990646v – reference: ShibataTFujimotoTYokotaKTakagiKIridium complex-catalyzed highly enantio- and diastereoselective [2+2+2] cycloaddition for the synthesis of axially chiral teraryl compoundsJ. Am. Chem. Soc.2004126838283831:CAS:528:DC%2BD2cXkvFyit7g%3D10.1021/ja048131d15237987 – reference: PhillipsEMChanAScheidtKADiscovering new reactions with N-heterocyclic carbene catalysisAldrichimica Acta20094255661:CAS:528:DC%2BC3cXktVSgsb8%3D210721302975109 – reference: GaoHPractical organocatalytic synthesis of functionalized non-C2-symmetrical atropisomeric biarylsAngew. Chem. Int. Ed.2016555665711:CAS:528:DC%2BC2MXhvVOlt7rK10.1002/anie.201508419 – reference: MakiBEChanAPhillipsEMScheidtKATandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenesOrg. Lett.200793713741:CAS:528:DC%2BD28Xhtlaks7%2FP10.1021/ol062940f17217307 – reference: MaGDengJSibiMPFluxionally chiral DMAP catalysts: kinetic resolution of axially chiral biaryl compoundsAngew. Chem. Int. Ed.20145311818118211:CAS:528:DC%2BC2cXhtlOmurrI10.1002/anie.201406684 – reference: EndersDBalensieferTNucleophilic carbenes in asymmetric organocatalysisAcc. Chem. Res.2004375345411:CAS:528:DC%2BD2cXisVequ7Y%3D10.1021/ar030050j15311952 – reference: MahatthananchaiJKaeobamrungJBodeJWChiral N-heterocyclic carbene-catalyzed annulations of enals and ynals with stable enols: a highly enantioselective Coates−Claisen rearrangementACS Catal.201224945031:CAS:528:DC%2BC38XjtVCqtrk%3D10.1021/cs300020t224682323314221 – reference: CandishLLevensALuptonDWN-heterocyclic carbene catalysed redox isomerisation of esters to functionalized benzaldehydesChem. Sci.20156236623701:CAS:528:DC%2BC2MXhsVGnsr8%3D10.1039/C4SC03726J293081505645917 – reference: MahatthananchaiJBodeJWOn the mechanism of N-heterocyclic carbene-catalyzed reactions involving acyl azoliumsAcc. Chem. Res.2014476967071:CAS:528:DC%2BC2cXlslCruw%3D%3D10.1021/ar400239v24410291 – reference: YamamotoTAkaiYNagataYSuginomeMHighly enantioselective synthesis of axially chiral biarylphosphonates: asymmetric Suzuki–Miyaura coupling using high-molecular-weight, helically chiral polyquinoxaline-based phosphinesAngew. Chem. Int. Ed.201150884488471:CAS:528:DC%2BC3MXpvVantrc%3D10.1002/anie.201103792 – reference: KaeobamrungJMahatthananchaiJZhengPBodeJWAn enantioselective claisen rearrangement catalyzed by N-heterocyclic carbenesJ. Am. Chem. Soc.2010132881088121:CAS:528:DC%2BC3cXnsFGmtLw%3D10.1021/ja103631u205501272902991 – reference: GuoFKonkolLCThomsonRJEnantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchangeJ. Am. Chem. Soc.201113318201:CAS:528:DC%2BC3cXhsFClur7K10.1021/ja108717r21141997 – reference: MeyersAWettlauferDThe complete intramolecular transfer of a central chiral element to an axial chiral element. Oxid. (S)-4-naphthyldihydroquinolines to (S)-4-naphthylquinolines J. Am. Chem. Soc.1984106113511361:CAS:528:DyaL2cXosFGksg%3D%3D10.1021/ja00316a063 – reference: MahatthananchaiJBodeJWThe effect of the N-mesityl group in NHC-catalyzed reactionsChem. Sci.201231921971:CAS:528:DC%2BC3MXhsFeisr%2FN10.1039/C1SC00397F23687565 – reference: ShenXJonesGOWatsonDABhayanaBBuchwaldSLEnantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki−Miyaura reaction: substrate scope and quantum mechanical investigationsJ. Am. Chem. Soc.201013211278112871:CAS:528:DC%2BC3cXptFOls7c%3D10.1021/ja104297g206986952924746 – reference: Bringmann, G., Gìnther, C., Ochse, M., Schupp, O. & Tasler, S. in Progress in the Chemistry of Organic Natural Products, Vol. 82 (eds. Herz, W., Falk, H., Kirby, G. W., Moore, R. E.) 1–129 (Springer, Berlin, 1998). – reference: HeMStrubleJRBodeJWHighly enantioselective azadiene Diels−Alder reactions catalyzed by chiral N-heterocyclic carbenesJ. Am. Chem. Soc.2006128841884201:CAS:528:DC%2BD28XlvFensbY%3D10.1021/ja062707c16802805 – reference: WannerBMahatthananchaiJBodeJWEnantioselective synthesis of dihydropyridinones via NHC-catalyzed Aza-Claisen reactionOrg. Lett.201113537853811:CAS:528:DC%2BC3MXhtFCgsLzN10.1021/ol202272t21905682 – reference: KozlowskiMCMorganBJLintonECTotal synthesis of chiral biaryl natural products by asymmetric biaryl couplingChem. Soc. Rev.200938319332071:CAS:528:DC%2BD1MXht12ht7rM10.1039/b821092f198473512904069 – reference: VorogushinAVWulffWDHansenHJStereoselectivity of the benzannulation reaction: efficient central-to-axial chirality transferJ. Am. Chem. Soc.2002124651265131:CAS:528:DC%2BD38Xjs1Ggtrg%3D10.1021/ja020150512047153 – reference: UozumiYMatsuuraYArakawaTYamadaYMAAsymmetric Suzuki–Miyaura coupling in water with a chiral palladium catalyst supported on an amphiphilic resinAngew. Chem. Int. Ed.200948270827101:CAS:528:DC%2BD1MXks1Clu7Y%3D10.1002/anie.200900469 – reference: RaupDEACardinal-DavidBHolteDScheidtKACooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactamsNat. Chem.201027667711:CAS:528:DC%2BC3cXhtVGmtbnN10.1038/nchem.727207298982928160 – reference: BreslowROn the mechanism of thiamine action. IV.1 Evidence from studies on model systemsJ. Am. Chem. Soc.195880371937261:CAS:528:DyaG1MXhslGqsA%3D%3D10.1021/ja01547a064 – reference: Wencel-DelordJPanossianALerouxFRColobertFRecent advances and new concepts for the synthesis of axially stereoenriched biarylsChem. Soc. Rev.201544341834301:CAS:528:DC%2BC2MXntVCisrk%3D10.1039/C5CS00012B25904287 – reference: YuCHuangHZhangYWangWDynamic kinetic resolution of biaryl lactones via a chiral bifunctional amine thiourea-catalyzed highly atropo-enantioselective transesterificationJ. Am. Chem. Soc.2016138695669581:CAS:528:DC%2BC28XosFSmtLg%3D10.1021/jacs.6b0360927218264 – volume: 111 start-page: 563 year: 2011 ident: 2952_CR3 publication-title: Chem. Rev. doi: 10.1021/cr100155e – volume: 23 start-page: 345 year: 1990 ident: 2952_CR5 publication-title: Acc. Chem. Res. doi: 10.1021/ar00178a005 – volume: 8 start-page: 15238 year: 2017 ident: 2952_CR25 publication-title: Nat. Commun. doi: 10.1038/ncomms15238 – volume: 106 start-page: 1135 year: 1984 ident: 2952_CR26 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00316a063 – volume: 48 start-page: 2708 year: 2009 ident: 2952_CR30 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200900469 – volume: 53 start-page: 5458 year: 2014 ident: 2952_CR15 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201402441 – volume: 42 start-page: 55 year: 2009 ident: 2952_CR37 publication-title: Aldrichimica Acta – ident: 2952_CR8 – volume: 52 start-page: 9293 year: 2013 ident: 2952_CR21 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201304039 – volume: 510 start-page: 485 year: 2014 ident: 2952_CR42 publication-title: Nature doi: 10.1038/nature13384 – ident: 2952_CR58 doi: 10.1021/ja027411v – volume: 53 start-page: 11818 year: 2014 ident: 2952_CR22 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201406684 – ident: 2952_CR1 – ident: 2952_CR11 doi: 10.1021/ja0319442 – volume: 124 start-page: 6512 year: 2002 ident: 2952_CR12 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0201505 – volume: 43 start-page: 3795 year: 2004 ident: 2952_CR34 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200454164 – volume: 13 start-page: 5378 year: 2011 ident: 2952_CR48 publication-title: Org. Lett. doi: 10.1021/ol202272t – volume: 52 start-page: 8592 year: 2013 ident: 2952_CR54 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201303247 – volume: 44 start-page: 5384 year: 2005 ident: 2952_CR6 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200462661 – volume: 55 start-page: 566 year: 2016 ident: 2952_CR20 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201508419 – volume: 131 start-page: 14176 year: 2009 ident: 2952_CR46 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja905501z – volume: 2 start-page: 494 year: 2012 ident: 2952_CR51 publication-title: ACS Catal. doi: 10.1021/cs300020t – volume: 133 start-page: 18 year: 2011 ident: 2952_CR13 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja108717r – volume: 41 start-page: 3511 year: 2012 ident: 2952_CR39 publication-title: Chem. Soc. Rev. doi: 10.1039/c2cs15333e – volume: 52 start-page: 14200 year: 2013 ident: 2952_CR19 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201308237 – volume: 138 start-page: 6956 year: 2016 ident: 2952_CR23 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.6b03609 – volume: 38 start-page: 3193 year: 2009 ident: 2952_CR2 publication-title: Chem. Soc. Rev. doi: 10.1039/b821092f – volume: 6 start-page: 505 year: 2011 ident: 2952_CR4 publication-title: ChemMedChem doi: 10.1002/cmdc.201000485 – volume: 135 start-page: 7414 year: 2013 ident: 2952_CR14 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja401709k – volume: 132 start-page: 1190 year: 2010 ident: 2952_CR53 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja910540j – volume: 29 start-page: 977 year: 1990 ident: 2952_CR9 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.199009771 – ident: 2952_CR65 – volume: 2 start-page: 766 year: 2010 ident: 2952_CR57 publication-title: Nat. Chem. doi: 10.1038/nchem.727 – volume: 137 start-page: 15062 year: 2015 ident: 2952_CR16 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.5b10152 – volume: 51 start-page: 9433 year: 2012 ident: 2952_CR49 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201204145 – volume: 9 start-page: 371 year: 2007 ident: 2952_CR52 publication-title: Org. Lett. doi: 10.1021/ol062940f – volume: 3 start-page: 192 year: 2012 ident: 2952_CR62 publication-title: Chem. Sci. doi: 10.1039/C1SC00397F – volume: 44 start-page: 3418 year: 2015 ident: 2952_CR7 publication-title: Chem. Soc. Rev. doi: 10.1039/C5CS00012B – volume: 63 start-page: 296 year: 1943 ident: 2952_CR63 publication-title: J. Pharm. Soc. Jpn. doi: 10.1248/yakushi1881.63.6_296 – volume: 50 start-page: 8844 year: 2011 ident: 2952_CR32 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201103792 – volume: 291 start-page: 77 year: 2009 ident: 2952_CR38 publication-title: Top. Curr. Chem. doi: 10.1007/128_2008_18 – volume: 49 start-page: 9266 year: 2010 ident: 2952_CR55 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201004593 – volume: 126 start-page: 8382 year: 2004 ident: 2952_CR35 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja048131d – ident: 2952_CR59 doi: 10.1021/jo050645n – volume: 15 start-page: 9307 year: 2015 ident: 2952_CR43 publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.5b00060 – volume: 6 start-page: 2366 year: 2015 ident: 2952_CR44 publication-title: Chem. Sci. doi: 10.1039/C4SC03726J – volume: 45 start-page: 1147 year: 2006 ident: 2952_CR17 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200503042 – volume: 37 start-page: 2 year: 2008 ident: 2952_CR61 publication-title: Chem. Lett. doi: 10.1246/cl.2008.2 – volume: 121 start-page: 8943 year: 1999 ident: 2952_CR29 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja990646v – volume: 132 start-page: 5345 year: 2010 ident: 2952_CR56 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja910666n – volume: 33 start-page: 1842 year: 1994 ident: 2952_CR10 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.199418421 – volume: 80 start-page: 3719 year: 1958 ident: 2952_CR64 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01547a064 – volume: 133 start-page: 4694 year: 2011 ident: 2952_CR47 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja111067j – volume: 132 start-page: 8810 year: 2010 ident: 2952_CR50 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja103631u – volume: 37 start-page: 534 year: 2004 ident: 2952_CR36 publication-title: Acc. Chem. Res. doi: 10.1021/ar030050j – volume: 8 start-page: 637 year: 2006 ident: 2952_CR45 publication-title: Org. Lett. doi: 10.1021/ol052826h – volume: 47 start-page: 696 year: 2014 ident: 2952_CR41 publication-title: Acc. Chem. Res. doi: 10.1021/ar400239v – volume: 7 start-page: 10677 year: 2016 ident: 2952_CR24 publication-title: Nat. Commun. doi: 10.1038/ncomms10677 – volume: 42 start-page: 4906 year: 2013 ident: 2952_CR40 publication-title: Chem. Soc. Rev. doi: 10.1039/c3cs35522e – volume: 122 start-page: 12051 year: 2000 ident: 2952_CR27 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja005622z – volume: 132 start-page: 11278 year: 2010 ident: 2952_CR31 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja104297g – volume: 134 start-page: 916 year: 2012 ident: 2952_CR18 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja211069f – volume: 128 start-page: 8418 year: 2006 ident: 2952_CR60 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja062707c – volume: 136 start-page: 570 year: 2014 ident: 2952_CR33 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja409669r – volume: 110 start-page: 8153 year: 1988 ident: 2952_CR28 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00232a030 |
| SSID | ssj0000391844 |
| Score | 2.5597937 |
| Snippet | Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric... Axially chiral compounds are commonly found in nature. Here, the authors show the highly enantioselective construction of axially chiral biaryls via an... |
| SourceID | doaj pubmedcentral proquest pubmed crossref springer |
| SourceType | Open Website Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 611 |
| SubjectTerms | 639/638/403/933 639/638/77/883 639/638/77/889 Active control Carbenes Catalysis Catalysts Chemical bonds Chemical reactions Chemical synthesis Diketones Enantiomers Humanities and Social Sciences Intermediates Lewis acid multidisciplinary Organic chemistry Oxidizing agents Science Science (multidisciplinary) Substrates Transformations |
| SummonAdditionalLinks | – databaseName: DOAJ Directory of Open Access Journals dbid: DOA link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3NS1wxEA9FEHopVfvxWpV38GaDeUlePo62KOLBk4pQSsgnLsiuuOth-9d3krxdd61tL70meS_JzGTml2Qyg9ABT4AC-qgxUSlhMAEB2ygJ5soxrz3vOlu8fC_E2RU_v-lvVlJ9ZZ-wGh64Eu7IW29FvgwTTnEbpLMpCO51DDKFPpQ4n2DzVjZTRQczDVsXPrySIUwdTXnRCaRTmFDdU8zWLFEJ2P8SyvzdWfLZjWkxRKdv0ZsBQbbHdeRb6FUcb6PNmlNyvoOuT7Jry2gyLQluQJe139kh-9HmM-_7ldL8RLj6wbXlCGf-M4bWzdsLfJs9ZCZ-7u9GHuoeXFaH79DV6cnltzM8JE_Avpdshi1h0ifAM0zZyGPokk86dsLq5KzlViogpvUdDcAbZyUV0gUhuRCBegUo5j3aGE_G8SNqk2Uwfdp7D5s1wr3lHP4UWJ8ojYCZGtQtCGn8EFk8J7i4M-WGmylTiW-A-KYQ37AGHS6_ua9xNf7a-mvmz7JljoldCkBSzCAp5l-S0qDdBXfNsFCnOQtnQcUUqj9URi97oRpkFxBpg-SaCKwNY71mPLotIbr7HGOIkwZ9WQjLU5d_nuan_zHNz-g1rVKOid5FG7OHx7gHwGnm9ssa-QXa6Rcq priority: 102 providerName: Directory of Open Access Journals – databaseName: ProQuest Technology Collection dbid: 8FG link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3dbxQhECdaY-KL8dut1eyDb5WUBRbYJ6OmZ-NDn6xpYgxhB7CXNLfn3flw_esdWO7q-dFXYPmYGYbfDsMMIa9lRBTQho4yEyPFI8BTFzSj0vQCOpBN47KX76k6OZOfztvzYnBbFrfKjU7MitoPkGzkR5yN8IWLt_MfNGWNSrerJYXGbXKnwZMmuXSZycetjSVFPzdSlrcyTJijpcyagTWGMt61nIqd8yiH7f8X1vzbZfKPe9N8HE0ekPsFR9bvRsY_JLfC7BG5O2aWXD8mX46Tg8t0WOY0N6jR6q_iUHyrk-V7_ltpeig8esPV2ZCzvgq-7tf1Kb1IfjIDrOFyCli36JNSfELOJsefP5zQkkKBQqvFijomNERENcK4IINvIsQuNMp1sXdOOm2c1w4a7pFDvdNc6d4rLZXyHAximadkbzbMwnNSRydw-bwFwF82JsFJiT150UbOAyKnijQbQloo8cVTmotLm--5hbEj8S0S32biW1GRw-038zG6xo2t3yf-bFumyNi5YFh8t2WjWXDgVLo8Vb2RuLjeRa8kdMHr6FuPnRxsuGvLdl3aa-GqyLOR0dtReIcSjLi0InpHBHamsVszm17kQN1tijQkWUXebITlesj_L3P_5hm-IPf4KL-UdQdkb7X4GV4iMFr1r7L0_wLEcgxq priority: 102 providerName: ProQuest – databaseName: HAS SpringerNature Open Access 2022 dbid: AAJSJ link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3NbxQhFCe1jYkXY_3qatvMwVslMsAAc1xNm2YPvdSaJsYQeIDdpNltdtfD-tf7YGZWV6uJVz6H9x7wG3j8HiFvZEIU0MSWMpMSxS0gUBc1o9J4AS3IunbFy_dCnV_JyXVzvUP48BamOO0XSsuyTA_eYe-WskxpVhvKeNtwKh6QvUzVjra9Nx5PLiebk5XMeW6k7F_IMGHuqby1CxWy_vsQ5p-Okr_dlpZN6OwJedyjx2rcfe8-2Ymzp-RhF09y_Yx8Os1uLdP5sgS3wXWs-ixOxJcqn3ff_ZKanwd3PnBVOb5Zf4-h8uvqgt5k75g5rOF2Cpi38HkpfE6uzk4_fjinfeAECo0WK-qY0JAQywjjooyhTpDaWCvXJu-cdNq4oB3UPKBevNNcaR-UlkoFDgYRzAuyO5vP4gGpkhM4fN4A4I8ak-CkxJaCaBLnEfHSiNSDIC30rOI5uMWtLbfbwthO-BaFb4vwrRiRk02du45T45-l32f9bEpmPuySMF98tb19WHDgVL4yVd5IHJx3KSgJbQw6hSZgI4eDdm0_SZc5AmdBxByzX3aK3vTCW7RbRKMjordMYOsztnNm05tCz91kfiHJRuTtYCw_u_z7MF_9X_HX5BHv7Jmy9pDsrhbf4hHCo5U_7ufDDx5oC8k priority: 102 providerName: Springer Nature |
| Title | Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes |
| URI | https://link.springer.com/article/10.1038/s41467-018-02952-3 https://www.ncbi.nlm.nih.gov/pubmed/29426851 https://www.proquest.com/docview/2000011523 https://pubmed.ncbi.nlm.nih.gov/PMC5807440 https://doaj.org/article/caca689026b84ad7bafd64c9ed7fd5d3 |
| Volume | 9 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1bixMxFA57QfBFvNt1LfPg2xqdyX0eRLqldSlYRK0URIZMLm6htGvbBcdf70lmplqtPvgyA7kn5yTnS3JyDkJPmQcUwF2OU-U9BhFgsXYyxUyV1OSGZZmOWr5jcTFhoymfHqDW3VEzgOu9W7vgT2qymj__9rV6BRP-Zf1kXL1Yszjd00zhlOScYHqIjkEyyeDR4E0D9-PKTHPY0LDm7cz-rME6cA5tVjzbEVXRov8-GPqnNuVvV6pRUg1vo1sNxEx6NU_cQQducRfdqJ1OVvfQx0HQfZkt19EDDix2ySd6Rj8n4VD86pfQ8Ia4VpRL4hlP9d3ZpKySMb4MKjRLU5n5zEDcqgzr5X00GQ4-9C9w410BGy7pBuuUSuMB8FClHXM288bnLhM696XWTEulrdQmIxaIV2pJhCytkEwIS4wCmPMAHS2WC_cIJV5T6D7hxsBuLmVGMwYlWco9IQ5AVQdl7UAWpjE9HjxgzIt4BU5VUdOhADoUkQ4F7aCzbZ6r2vDGP1OfB_psUwaj2TFgufpSNHOwMNpoEe5VRakYdK7U3gpmcmelt9xCIactdYuWEYObzgibCUQ_rAm9raVllA6SOyyw04zdmMXsMtrw5sEIEUs76FnLLD-r_Hs3T_67osfoJqm5HKf5KTrarK7dE4BTm7KLDuVUwlcNX3fRca83ej-C__lg_PYdhPZFvxsPKrpxLv0A820j6A |
| linkProvider | Scholars Portal |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtR3LbtQwcFQVIbgg3gQK5ACnYjWxndg5IMSjy5aWPbWoEkLG8YOuVO0uu4tQ-Ci-kbGTbFkevfVqJ36MxzPjeQI84R6lgMJVJJPeE2QBlmgnMsJlzUxleJ7r6OU7KodH_N1xcbwBP_tYmOBW2dPESKjt1AQd-Q7NWvGFshezryRUjQrW1b6ERosW-675jk-2xfO9N3i-Tykd7B6-HpKuqgAxhWBLojMmjEdGz6R23NncG1-5vNSVr7XmWkhthTY5tbjoWgtaitqWgpelpUbKkHwJSf4lzpCTh8j0wduVTidkW5ecd7E5OMHOgkdKlOWSZLQqKGFr_C-WCfiXbPu3i-YfdtrI_gbX4Vont6YvW0S7ARtuchMut5Usm1vwYTc41Iyni1hWBylo-pFts09p0LTPfmsNgcmt910aFUfND2fTuklH5CT45UxNY07HBvvmdSDCt-HoQoB7BzYn04m7B6nXDLdPC2PwiZhxoznHkSwrPKUOJbUE8h6QynT5zENZjVMV7epMqhb4CoGvIvAVS2B79c-szeZx7tevwvmsvgyZuGPDdP5FdRdbGW10GYy1ZS05bq7W3pbcVM4KbwuLg2z1p6s68rBQZ8icwN32oFez0ApvDMrBCYg1FFhbxnrPZHwSE4MXIbMRzxJ41iPL2ZT_3-b981f4GK4MD98fqIO90f4DuEpbXCZZtQWby_k39xCFsmX9KN6EFD5f9NX7BcthS2o |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtR1db9Mw8DR1AvGC-CZjQB7gaVhNbCdOHhBirNXGUDUhhiYhZBx_sEpT27VFKPw0fh1nJ-koH3vbq53Yvu-zfb4DeMYdegGZLUlSOEfQBBiirEgILyqmS83TVIUo31G-f8zfnmQnG_Czewvjwyo7nRgUtZlqf0bep0njvlDWd21YxNHe8NXsnPgKUv6mtSun0bDIoa2_4_Zt8fJgD2n9nNLh4MObfdJWGCA6E2xJVMKEdmj0WaEstyZ12pU2zVXpKqW4EoUyQumUGgSgUoLmojK54HluqC4Kn4gJ1f-m8LuiHmzuDkZH71cnPD73esF5-1IHp-gveNBLSVqQhJYZJWzNGoaiAf_ydP8O2Pzj1jYYw-EtuNl6sfHrhu1uw4ad3IFrTV3L-i58HPjwmvF0EYrsoD6NP7Ed9jn25-6z31r9M-UmFi8Ox0j1D2viqo5H5NRH6Ux1rc_GGvvmlVfJ9-D4StB7H3qT6cQ-hNgphuDTTGvcMCZcK85xJMMyR6lFvy2CtEOk1G12c19k40yGW3ZWyAb5EpEvA_Ili2Bn9c-sye1x6de7nj6rL31e7tAwnX-VrZhLrbTK_dVtXhUcgauUMznXpTXCmczgINsddWWrLBbygrUjeNAQejULLVF-0CuOQKyxwNoy1nsm49OQJjzzeY54EsGLjlkupvw_mFuXr_ApXEexk-8ORoeP4AZtWJkk5Tb0lvNv9jF6aMvqSSsKMXy5aun7BZrYUPw |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Enantioselective+%5B3%2B3%5D+atroposelective+annulation+catalyzed+by+N-heterocyclic+carbenes&rft.jtitle=Nature+communications&rft.au=Zhao%2C+Changgui&rft.au=Guo%2C+Donghui&rft.au=Munkerup%2C+Kristin&rft.au=Huang%2C+Kuo-Wei&rft.date=2018-02-09&rft.pub=Nature+Publishing+Group+UK&rft.eissn=2041-1723&rft.volume=9&rft_id=info:doi/10.1038%2Fs41467-018-02952-3&rft_id=info%3Apmid%2F29426851&rft.externalDocID=PMC5807440 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2041-1723&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2041-1723&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2041-1723&client=summon |