Asymmetric Yttrium‐Catalyzed C(sp3)−H Addition of 2‐Methyl Azaarenes to Cyclopropenes
An enantioselective C−H addition to a C=C bond represents the most atom‐efficient route for the construction of chiral carbon–carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium‐catalyzed C(sp3)−H bond addition of 2‐methyl azaarenes, such as...
Saved in:
| Published in | Angewandte Chemie International Edition Vol. 56; no. 31; pp. 9207 - 9210 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Wiley Subscription Services, Inc
24.07.2017
|
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | An enantioselective C−H addition to a C=C bond represents the most atom‐efficient route for the construction of chiral carbon–carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium‐catalyzed C(sp3)−H bond addition of 2‐methyl azaarenes, such as 2‐methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl‐functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee).
Enantioselective C(sp3)−H bond additions of 2‐methyl azaarenes, such as 2‐methylpyridines, to substituted cyclopropenes and norbornenes have been achieved by using a chiral half‐sandwich yttrium catalyst. This process afforded a series of chiral pyridylmethyl‐functionalized cyclopropane and norbornane derivatives in good yields, high enantioselectivity, and 100 % atom efficiency. |
|---|---|
| AbstractList | An enantioselective C-H addition to a C=C bond represents the most atom-efficient route for the construction of chiral carbon-carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium-catalyzed C(sp3)-H bond addition of 2-methyl azaarenes, such as 2-methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl-functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97% ee). An enantioselective C−H addition to a C=C bond represents the most atom‐efficient route for the construction of chiral carbon–carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium‐catalyzed C(sp3)−H bond addition of 2‐methyl azaarenes, such as 2‐methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl‐functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee). Enantioselective C(sp3)−H bond additions of 2‐methyl azaarenes, such as 2‐methylpyridines, to substituted cyclopropenes and norbornenes have been achieved by using a chiral half‐sandwich yttrium catalyst. This process afforded a series of chiral pyridylmethyl‐functionalized cyclopropane and norbornane derivatives in good yields, high enantioselectivity, and 100 % atom efficiency. An enantioselective C-H addition to a C=C bond represents the most atom-efficient route for the construction of chiral carbon-carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium-catalyzed C(sp3 )-H bond addition of 2-methyl azaarenes, such as 2-methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl-functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee).An enantioselective C-H addition to a C=C bond represents the most atom-efficient route for the construction of chiral carbon-carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium-catalyzed C(sp3 )-H bond addition of 2-methyl azaarenes, such as 2-methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl-functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee). An enantioselective C-H addition to a C=C bond represents the most atom-efficient route for the construction of chiral carbon-carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium-catalyzed C(sp )-H bond addition of 2-methyl azaarenes, such as 2-methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl-functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee). An enantioselective C−H addition to a C=C bond represents the most atom‐efficient route for the construction of chiral carbon–carbon skeletons, a central research topic in organic synthesis. We herein report the enantioselective yttrium‐catalyzed C(sp 3 )−H bond addition of 2‐methyl azaarenes, such as 2‐methyl pyridines, to various substituted cyclopropenes and norbornenes. This process efficiently afforded a new family of chiral pyridylmethyl‐functionalized cyclopropane and norbornane derivatives in high yields and high enantioselectivities (up to 97 % ee ). |
| Author | Luo, Yong Hou, Zhaomin Teng, Huai‐Long Nishiura, Masayoshi |
| Author_xml | – sequence: 1 givenname: Yong surname: Luo fullname: Luo, Yong organization: RIKEN – sequence: 2 givenname: Huai‐Long surname: Teng fullname: Teng, Huai‐Long organization: RIKEN Center for Sustainable Resource Science – sequence: 3 givenname: Masayoshi surname: Nishiura fullname: Nishiura, Masayoshi organization: RIKEN Center for Sustainable Resource Science – sequence: 4 givenname: Zhaomin orcidid: 0000-0003-2841-5120 surname: Hou fullname: Hou, Zhaomin email: houz@riken.jp organization: RIKEN Center for Sustainable Resource Science |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28612990$$D View this record in MEDLINE/PubMed |
| BookMark | eNqFkT1rHDEQhkVwiD-SNmVYcGMXd9HXSqtyWRzb4NhNUoQUYk6rJTK7q7OkxayrlClDfqJ_SXScnYDBuJpBPM9omHcf7Yx-tAi9J3hJMKYfYXR2STGRuOSMvEJ7pKRkwaRkO7nnjC1kVZJdtB_jdearCos3aJdWglCl8B76Xsd5GGwKzhTfUi7TcP_zdwMJ-vnOtkVzFNfs-P7Xn7OibluXnB8L3xU0Q59t-jH3RX0HEOxoY5F80cym9-vg15uHt-h1B3207x7qAfr66eRLc7a4uDo9b-qLheFS5GVBlUqCJCtqWsME6wgBQemKlS1pFWfASFUpWdKVMLYzwJkorZS0Ai4IUHaAjrZz88c3k41JDy4a2_cwWj9FTRRWkrNKqIwePkGv_RTGvF2miFKMCywy9eGBmlaDbfU6uAHCrB_PlgG-BUzwMQbbaeMSbI6TArheE6w36ehNOvpfOllbPtEeJz8rqK1w63o7v0Dr-vL85L_7F2yMosI |
| CitedBy_id | crossref_primary_10_1039_C8OB01187G crossref_primary_10_1002_ange_202010489 crossref_primary_10_1002_ange_202013516 crossref_primary_10_1002_anie_202115996 crossref_primary_10_1021_jacs_1c10743 crossref_primary_10_1039_D2TA08542A crossref_primary_10_1021_acs_joc_7b02375 crossref_primary_10_1039_C7OB02068F crossref_primary_10_1021_acscatal_8b01189 crossref_primary_10_1002_ange_201711291 crossref_primary_10_1002_anie_201913060 crossref_primary_10_1021_jacs_4c09067 crossref_primary_10_1021_acs_inorgchem_4c05543 crossref_primary_10_1039_D1CC00181G crossref_primary_10_1002_anie_202210624 crossref_primary_10_1039_D0OB01499K crossref_primary_10_1002_ange_202502665 crossref_primary_10_1039_D1SC03476F crossref_primary_10_1002_anie_201904994 crossref_primary_10_1021_acsomega_2c05855 crossref_primary_10_1002_ange_201710128 crossref_primary_10_1021_acs_inorgchem_8b02067 crossref_primary_10_1039_C9CC09584E crossref_primary_10_1002_ange_202412456 crossref_primary_10_1021_jacs_1c00939 crossref_primary_10_1002_anie_202306511 crossref_primary_10_1002_chem_201900565 crossref_primary_10_1002_slct_202402042 crossref_primary_10_1038_s41467_024_50689_z crossref_primary_10_1039_D3QO00559C crossref_primary_10_1002_ange_201802244 crossref_primary_10_1016_j_xcrp_2023_101246 crossref_primary_10_1002_ange_202318203 crossref_primary_10_1002_ange_201807493 crossref_primary_10_1021_jacs_4c06899 crossref_primary_10_1002_ange_201904994 crossref_primary_10_1021_jacs_9b12503 crossref_primary_10_1021_acscatal_9b04960 crossref_primary_10_1039_D3DT01714A crossref_primary_10_1002_anie_202210560 crossref_primary_10_1007_s11426_023_1588_8 crossref_primary_10_1002_anie_202419567 crossref_primary_10_1002_ange_201913794 crossref_primary_10_1080_10426507_2019_1602773 crossref_primary_10_1021_acs_chemrev_8b00304 crossref_primary_10_1002_ajoc_202000193 crossref_primary_10_1002_ajoc_201900363 crossref_primary_10_1021_jacs_0c08362 crossref_primary_10_1021_acscatal_1c05546 crossref_primary_10_1021_acs_orglett_0c01833 crossref_primary_10_1002_ejoc_202000752 crossref_primary_10_1246_cl_180132 crossref_primary_10_1002_anie_201913794 crossref_primary_10_1002_ange_202210624 crossref_primary_10_1002_ange_202308488 crossref_primary_10_1002_ange_202419567 crossref_primary_10_1021_jacs_0c13166 crossref_primary_10_1002_anie_202502665 crossref_primary_10_1016_j_trechm_2022_01_005 crossref_primary_10_1021_jacs_4c17210 crossref_primary_10_1039_D0CC05219A crossref_primary_10_1021_acscatal_2c04396 crossref_primary_10_1002_anie_201807493 crossref_primary_10_1002_chem_201902817 crossref_primary_10_1021_jacs_0c01171 crossref_primary_10_1021_jacs_9b04275 crossref_primary_10_1002_cctc_202201083 crossref_primary_10_1016_j_checat_2022_08_008 crossref_primary_10_1002_anie_201802244 crossref_primary_10_1002_anie_201710128 crossref_primary_10_1002_asia_202000089 crossref_primary_10_1002_anie_202308488 crossref_primary_10_1002_ange_202306511 crossref_primary_10_1002_ajoc_202200720 crossref_primary_10_1021_acs_organomet_8b00397 crossref_primary_10_1039_D0CC01612H crossref_primary_10_1002_anie_202013516 crossref_primary_10_1039_C9DT04338A crossref_primary_10_1039_D2RA02180C crossref_primary_10_1002_anie_202010489 crossref_primary_10_1016_j_mencom_2022_11_023 crossref_primary_10_1002_ange_202115996 crossref_primary_10_1021_acs_inorgchem_2c02953 crossref_primary_10_1002_ange_201809680 crossref_primary_10_1021_acs_joc_0c03054 crossref_primary_10_1002_anie_202318203 crossref_primary_10_1002_anie_201711291 crossref_primary_10_1016_j_ccr_2018_05_013 crossref_primary_10_1002_ange_201913060 crossref_primary_10_1002_ange_202210560 crossref_primary_10_1002_chem_202101179 crossref_primary_10_1002_anie_202218798 crossref_primary_10_1002_ange_202306381 crossref_primary_10_1021_acscatal_9b02623 crossref_primary_10_5059_yukigoseikyokaishi_78_575 crossref_primary_10_1021_acscatal_2c02193 crossref_primary_10_6023_cjoc202308007 crossref_primary_10_1002_ange_202012122 crossref_primary_10_1002_cjoc_202200176 crossref_primary_10_1021_acs_joc_8b03170 crossref_primary_10_1021_acscatal_2c03681 crossref_primary_10_1002_ange_202218798 crossref_primary_10_1039_D2CC02489F crossref_primary_10_1002_ange_201713324 crossref_primary_10_1002_adsc_202000782 crossref_primary_10_1021_jacs_3c06482 crossref_primary_10_1021_acs_orglett_0c04060 crossref_primary_10_1002_anie_202008166 crossref_primary_10_1039_D2GC04296G crossref_primary_10_1016_j_tetlet_2018_10_014 crossref_primary_10_1021_acs_orglett_1c03404 crossref_primary_10_1007_s11172_024_4271_1 crossref_primary_10_1002_anie_202412456 crossref_primary_10_1021_jacs_4c02144 crossref_primary_10_1039_D1QO00627D crossref_primary_10_1002_anie_202306381 crossref_primary_10_1002_anie_202012122 crossref_primary_10_1016_j_tet_2022_132629 crossref_primary_10_1002_anie_201809680 crossref_primary_10_1002_ejoc_201901899 crossref_primary_10_1002_chem_202001814 crossref_primary_10_1016_j_ccr_2018_08_017 crossref_primary_10_1002_anie_201713324 crossref_primary_10_1039_C9OB01559K crossref_primary_10_1021_acscatal_4c05026 crossref_primary_10_1002_ange_202008166 crossref_primary_10_1021_jacs_7b10786 |
| Cites_doi | 10.1021/acs.accounts.5b00219 10.1002/anie.199609711 10.1002/ange.19961080907 10.1002/ange.201609853 10.1016/j.bmc.2015.09.031 10.1039/C1CS15154A 10.1002/anie.201005215 10.1021/jo9806299 10.1002/anie.201106155 10.1021/ja107738a 10.1021/cr0100188 10.1021/ja0496928 10.1021/acs.accounts.5b00016 10.1021/acs.chemrev.5b00138 10.1021/acs.accounts.6b00051 10.1016/j.tet.2012.08.071 10.1021/ja905213f 10.1016/j.tet.2008.04.079 10.1021/ja805059f 10.1021/cr050988l 10.1002/chem.201501121 10.1002/anie.201609853 10.1021/ja208129t 10.1021/acs.accounts.6b00070 10.1002/ange.201208867 10.1021/acs.chemrev.6b00599 10.1021/ol1029904 10.1002/ange.201309886 10.1021/acs.chemrev.6b00798 10.1021/cr010007e 10.1002/ange.201206233 10.1002/anie.201701094 10.1039/c0dt01229g 10.1039/C5CC07102J 10.1021/ja034210y 10.1039/c1cs15074j 10.1002/anie.201208867 10.1002/anie.201609065 10.1039/c2cs35067j 10.1039/C6SC00833J 10.1021/ja510419z 10.1021/jacs.6b03859 10.1002/ange.201701094 10.1021/ja103786c 10.1021/ja211945m 10.1002/anie.201309886 10.1021/ja504995f 10.1039/C4QO00157E 10.1002/anie.201206233 10.1002/ange.201005215 10.1002/ange.201106155 10.1021/ja803523z 10.1039/c0cc01265c 10.1039/np9971400637 10.1021/jacs.5b11220 10.1021/ol201907w 10.1002/ange.201609065 |
| ContentType | Journal Article |
| Copyright | 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
| Copyright_xml | – notice: 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim – notice: 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. – notice: 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
| DBID | AAYXX CITATION NPM 7TM K9. 7X8 |
| DOI | 10.1002/anie.201705431 |
| DatabaseName | CrossRef PubMed Nucleic Acids Abstracts ProQuest Health & Medical Complete (Alumni) MEDLINE - Academic |
| DatabaseTitle | CrossRef PubMed ProQuest Health & Medical Complete (Alumni) Nucleic Acids Abstracts MEDLINE - Academic |
| DatabaseTitleList | ProQuest Health & Medical Complete (Alumni) MEDLINE - Academic PubMed CrossRef |
| Database_xml | – sequence: 1 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 |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1521-3773 |
| Edition | International ed. in English |
| EndPage | 9210 |
| ExternalDocumentID | 28612990 10_1002_anie_201705431 ANIE201705431 |
| Genre | shortCommunication Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: Japan Society for the Promotion of Science funderid: 26220802 |
| GroupedDBID | --- -DZ -~X .3N .GA 05W 0R~ 10A 1L6 1OB 1OC 1ZS 23M 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5RE 5VS 66C 6TJ 702 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHHS AAHQN AAMNL AANLZ AAONW AASGY AAXRX AAYCA AAZKR ABCQN ABCUV ABEML ABIJN ABLJU ABPPZ ABPVW ACAHQ ACCFJ ACCZN ACFBH ACGFS ACIWK ACNCT ACPOU ACPRK ACSCC ACXBN ACXQS ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFRAH AFWVQ AFZJQ AHBTC AHMBA AITYG AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN ALVPJ AMBMR AMYDB ATUGU AUFTA AZBYB AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BTSUX BY8 CS3 D-E D-F D0L DCZOG DPXWK DR1 DR2 DRFUL DRSTM EBS EJD F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HBH HGLYW HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES M53 MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- OIG P2P P2W P2X P4D PQQKQ Q.N Q11 QB0 QRW R.K RNS ROL RWI RX1 RYL SUPJJ TN5 UB1 UPT V2E VQA W8V W99 WBFHL WBKPD WH7 WIB WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XPP XSW XV2 YZZ ZZTAW ~IA ~KM ~WT AAYXX ABDBF ABJNI AETEA AEYWJ AGHNM AGYGG CITATION NPM 7TM K9. 7X8 |
| ID | FETCH-LOGICAL-c4761-3a9597a71b2cdc363f11a622b35d1d943a31889752b6cefca4365e7728a461a23 |
| IEDL.DBID | DR2 |
| ISSN | 1433-7851 1521-3773 |
| IngestDate | Fri Jul 11 08:21:18 EDT 2025 Fri Jul 25 10:12:28 EDT 2025 Thu Apr 03 07:05:45 EDT 2025 Thu Apr 24 22:53:16 EDT 2025 Tue Jul 01 02:26:05 EDT 2025 Wed Jan 22 16:31:25 EST 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 31 |
| Keywords | norbornenes cyclopropenes pyridines asymmetric catalysis yttrium catalysis |
| Language | English |
| License | http://onlinelibrary.wiley.com/termsAndConditions#vor 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c4761-3a9597a71b2cdc363f11a622b35d1d943a31889752b6cefca4365e7728a461a23 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
| ORCID | 0000-0003-2841-5120 |
| PMID | 28612990 |
| PQID | 1919934606 |
| PQPubID | 946352 |
| PageCount | 4 |
| ParticipantIDs | proquest_miscellaneous_1909743869 proquest_journals_1919934606 pubmed_primary_28612990 crossref_citationtrail_10_1002_anie_201705431 crossref_primary_10_1002_anie_201705431 wiley_primary_10_1002_anie_201705431_ANIE201705431 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | July 24, 2017 |
| PublicationDateYYYYMMDD | 2017-07-24 |
| PublicationDate_xml | – month: 07 year: 2017 text: July 24, 2017 day: 24 |
| PublicationDecade | 2010 |
| PublicationPlace | Germany |
| PublicationPlace_xml | – name: Germany – name: Weinheim |
| PublicationTitle | Angewandte Chemie International Edition |
| PublicationTitleAlternate | Angew Chem Int Ed Engl |
| PublicationYear | 2017 |
| Publisher | Wiley Subscription Services, Inc |
| Publisher_xml | – name: Wiley Subscription Services, Inc |
| References | 2014 2014; 53 126 2007; 107 2004; 126 2015; 51 2011; 40 2011; 13 2017 2017; 56 129 2009; 131 1998; 63 2014; 136 2011; 133 2013 2013; 52 125 2014; 1 2015; 48 2016; 7 2016 2016; 55 128 1996 1996; 35 108 2012; 134 2010; 46 2015; 115 2015; 137 2012 2012; 51 124 1997; 14 2015; 21 2010; 132 2011 2011; 50 123 2016; 138 2014 2008; 64 2003; 103 2003; 125 2012; 68 2016; 49 2008; 130 2016; 24 2012; 41 e_1_2_2_4_1 e_1_2_2_24_2 e_1_2_2_47_2 e_1_2_2_22_2 e_1_2_2_49_2 e_1_2_2_6_2 e_1_2_2_20_2 e_1_2_2_2_2 e_1_2_2_41_1 e_1_2_2_28_2 e_1_2_2_43_2 e_1_2_2_8_1 e_1_2_2_26_3 e_1_2_2_26_2 e_1_2_2_45_2 e_1_2_2_13_2 e_1_2_2_36_2 e_1_2_2_59_1 e_1_2_2_11_2 e_1_2_2_38_2 e_1_2_2_51_2 e_1_2_2_19_2 e_1_2_2_30_2 e_1_2_2_53_2 e_1_2_2_32_1 e_1_2_2_51_3 e_1_2_2_17_2 e_1_2_2_55_2 e_1_2_2_34_2 e_1_2_2_15_1 e_1_2_2_34_3 e_1_2_2_57_1 e_1_2_2_3_2 e_1_2_2_23_2 e_1_2_2_48_2 e_1_2_2_5_2 e_1_2_2_21_3 e_1_2_2_5_3 e_1_2_2_21_2 e_1_2_2_1_1 e_1_2_2_40_1 e_1_2_2_29_2 e_1_2_2_42_2 e_1_2_2_7_2 e_1_2_2_44_2 e_1_2_2_9_3 e_1_2_2_25_3 e_1_2_2_27_1 e_1_2_2_46_1 e_1_2_2_9_2 e_1_2_2_25_2 Bartoli G. (e_1_2_2_12_2) 2014 e_1_2_2_35_3 e_1_2_2_37_2 e_1_2_2_10_2 e_1_2_2_39_2 e_1_2_2_39_3 e_1_2_2_50_2 e_1_2_2_31_1 e_1_2_2_18_2 e_1_2_2_52_2 e_1_2_2_56_1 e_1_2_2_16_2 e_1_2_2_33_2 e_1_2_2_54_2 e_1_2_2_58_1 e_1_2_2_14_2 e_1_2_2_35_2 |
| References_xml | – volume: 107 start-page: 3117 year: 2007 publication-title: Chem. Rev. – volume: 40 start-page: 5534 year: 2011 publication-title: Chem. Soc. Rev. – volume: 50 123 start-page: 2144 2192 year: 2011 2011 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 13 start-page: 4692 year: 2011 publication-title: Org. Lett. – volume: 125 start-page: 7198 year: 2003 publication-title: J. Am. Chem. Soc. – volume: 68 start-page: 9009 year: 2012 publication-title: Tetrahedron – volume: 49 start-page: 2080 year: 2016 publication-title: Acc. Chem. Res. – volume: 7 start-page: 5265 year: 2016 publication-title: Chem. Sci. – volume: 126 start-page: 3688 year: 2004 publication-title: J. Am. Chem. Soc. – volume: 55 128 start-page: 15406 15632 year: 2016 2016 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 131 start-page: 13226 year: 2009 publication-title: J. Am. Chem. Soc. – volume: 51 start-page: 16660 year: 2015 publication-title: Chem. Commun. – volume: 138 start-page: 6147 year: 2016 publication-title: J. Am. Chem. Soc. – volume: 132 start-page: 11847 year: 2010 publication-title: J. Am. Chem. Soc. – volume: 103 start-page: 1625 year: 2003 publication-title: Chem. Rev. – volume: 56 129 start-page: 6783 6887 year: 2017 2017 end-page: 6787 6891 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 41 start-page: 2222 year: 2012 publication-title: Chem. Soc. Rev. – volume: 137 start-page: 15414 year: 2015 publication-title: J. Am. Chem. Soc. – volume: 46 start-page: 6296 year: 2010 publication-title: Chem. Commun. – volume: 41 start-page: 4631 year: 2012 publication-title: Chem. Soc. Rev. – volume: 64 start-page: 7041 year: 2008 publication-title: Tetrahedron – volume: 35 108 start-page: 971 1049 year: 1996 1996 publication-title: Angew. Chem. Int. Ed. Engl. Angew. Chem. – volume: 51 124 start-page: 12828 13000 year: 2012 2012 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 1 start-page: 1116 year: 2014 publication-title: Org. Chem. Front. – volume: 48 start-page: 2209 year: 2015 publication-title: Acc. Chem. Res. – volume: 48 start-page: 1021 year: 2015 publication-title: Acc. Chem. Res. – volume: 115 start-page: 9410 year: 2015 publication-title: Chem. Rev. – volume: 136 start-page: 15833 year: 2014 publication-title: J. Am. Chem. Soc. – volume: 40 start-page: 1547 year: 2011 publication-title: Dalton Trans. – volume: 63 start-page: 5533 year: 1998 publication-title: J. Org. Chem. – volume: 14 start-page: 637 year: 1997 publication-title: Nat. Prod. Rep. – volume: 49 start-page: 922 year: 2016 publication-title: Acc. Chem. Res. – volume: 103 start-page: 977 year: 2003 publication-title: Chem. Rev. – volume: 52 125 start-page: 4418 4514 year: 2013 2013 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 53 126 start-page: 5504 5608 year: 2014 2014 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 133 start-page: 18086 year: 2011 publication-title: J. Am. Chem. Soc. – volume: 130 start-page: 12220 year: 2008 publication-title: J. Am. Chem. Soc. – volume: 134 start-page: 3300 year: 2012 publication-title: J. Am. Chem. Soc. – volume: 130 start-page: 13804 year: 2008 publication-title: J. Am. Chem. Soc. – volume: 55 128 start-page: 14812 15032 year: 2016 2016 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 136 start-page: 12209 year: 2014 publication-title: J. Am. Chem. Soc. – volume: 24 start-page: 342 year: 2016 publication-title: Bioorg. Med. Chem. – volume: 50 123 start-page: 12626 12834 year: 2011 2011 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 13 start-page: 819 year: 2011 publication-title: Org. Lett. – volume: 21 start-page: 8394 year: 2015 publication-title: Chem. Eur. J. – start-page: 979 year: 2014 publication-title: Synthesis – volume: 132 start-page: 16354 year: 2010 publication-title: J. Am. Chem. Soc. – ident: e_1_2_2_46_1 – ident: e_1_2_2_31_1 doi: 10.1021/acs.accounts.5b00219 – ident: e_1_2_2_9_2 doi: 10.1002/anie.199609711 – ident: e_1_2_2_9_3 doi: 10.1002/ange.19961080907 – ident: e_1_2_2_32_1 – ident: e_1_2_2_25_3 doi: 10.1002/ange.201609853 – ident: e_1_2_2_45_2 doi: 10.1016/j.bmc.2015.09.031 – ident: e_1_2_2_43_2 doi: 10.1039/C1CS15154A – ident: e_1_2_2_51_2 doi: 10.1002/anie.201005215 – ident: e_1_2_2_59_1 doi: 10.1021/jo9806299 – ident: e_1_2_2_21_2 doi: 10.1002/anie.201106155 – ident: e_1_2_2_19_2 doi: 10.1021/ja107738a – ident: e_1_2_2_2_2 doi: 10.1021/cr0100188 – ident: e_1_2_2_17_2 doi: 10.1021/ja0496928 – ident: e_1_2_2_30_2 doi: 10.1021/acs.accounts.5b00016 – ident: e_1_2_2_6_2 doi: 10.1021/acs.chemrev.5b00138 – ident: e_1_2_2_44_2 doi: 10.1021/acs.accounts.6b00051 – ident: e_1_2_2_15_1 – ident: e_1_2_2_54_2 doi: 10.1016/j.tet.2012.08.071 – ident: e_1_2_2_4_1 – ident: e_1_2_2_47_2 doi: 10.1021/ja905213f – ident: e_1_2_2_11_2 doi: 10.1016/j.tet.2008.04.079 – ident: e_1_2_2_18_2 doi: 10.1021/ja805059f – ident: e_1_2_2_28_2 doi: 10.1021/cr050988l – ident: e_1_2_2_36_2 doi: 10.1002/chem.201501121 – ident: e_1_2_2_25_2 doi: 10.1002/anie.201609853 – ident: e_1_2_2_33_2 doi: 10.1021/ja208129t – ident: e_1_2_2_13_2 doi: 10.1021/acs.accounts.6b00070 – ident: e_1_2_2_41_1 – ident: e_1_2_2_35_3 doi: 10.1002/ange.201208867 – ident: e_1_2_2_1_1 – ident: e_1_2_2_7_2 doi: 10.1021/acs.chemrev.6b00599 – ident: e_1_2_2_20_2 doi: 10.1021/ol1029904 – ident: e_1_2_2_57_1 – ident: e_1_2_2_5_3 doi: 10.1002/ange.201309886 – ident: e_1_2_2_14_2 doi: 10.1021/acs.chemrev.6b00798 – ident: e_1_2_2_27_1 – ident: e_1_2_2_10_2 doi: 10.1021/cr010007e – ident: e_1_2_2_34_3 doi: 10.1002/ange.201206233 – ident: e_1_2_2_26_2 doi: 10.1002/anie.201701094 – ident: e_1_2_2_50_2 doi: 10.1039/c0dt01229g – ident: e_1_2_2_55_2 doi: 10.1039/C5CC07102J – ident: e_1_2_2_16_2 doi: 10.1021/ja034210y – start-page: 979 year: 2014 ident: e_1_2_2_12_2 publication-title: Synthesis – ident: e_1_2_2_29_2 doi: 10.1039/c1cs15074j – ident: e_1_2_2_35_2 doi: 10.1002/anie.201208867 – ident: e_1_2_2_39_2 doi: 10.1002/anie.201609065 – ident: e_1_2_2_3_2 doi: 10.1039/c2cs35067j – ident: e_1_2_2_37_2 doi: 10.1039/C6SC00833J – ident: e_1_2_2_23_2 doi: 10.1021/ja510419z – ident: e_1_2_2_38_2 doi: 10.1021/jacs.6b03859 – ident: e_1_2_2_26_3 doi: 10.1002/ange.201701094 – ident: e_1_2_2_56_1 – ident: e_1_2_2_48_2 doi: 10.1021/ja103786c – ident: e_1_2_2_53_2 doi: 10.1021/ja211945m – ident: e_1_2_2_5_2 doi: 10.1002/anie.201309886 – ident: e_1_2_2_40_1 doi: 10.1021/ja504995f – ident: e_1_2_2_22_2 doi: 10.1039/C4QO00157E – ident: e_1_2_2_34_2 doi: 10.1002/anie.201206233 – ident: e_1_2_2_8_1 – ident: e_1_2_2_51_3 doi: 10.1002/ange.201005215 – ident: e_1_2_2_21_3 doi: 10.1002/ange.201106155 – ident: e_1_2_2_58_1 doi: 10.1021/ja803523z – ident: e_1_2_2_49_2 doi: 10.1039/c0cc01265c – ident: e_1_2_2_42_2 doi: 10.1039/np9971400637 – ident: e_1_2_2_24_2 doi: 10.1021/jacs.5b11220 – ident: e_1_2_2_52_2 doi: 10.1021/ol201907w – ident: e_1_2_2_39_3 doi: 10.1002/ange.201609065 |
| SSID | ssj0028806 |
| Score | 2.532228 |
| Snippet | An enantioselective C−H addition to a C=C bond represents the most atom‐efficient route for the construction of chiral carbon–carbon skeletons, a central... An enantioselective C-H addition to a C=C bond represents the most atom-efficient route for the construction of chiral carbon-carbon skeletons, a central... |
| SourceID | proquest pubmed crossref wiley |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 9207 |
| SubjectTerms | asymmetric catalysis Chemical synthesis Cyclopropane cyclopropenes Enantiomers Hydrogen bonds norbornenes Organic compounds Pyridines Yttrium yttrium catalysis |
| Title | Asymmetric Yttrium‐Catalyzed C(sp3)−H Addition of 2‐Methyl Azaarenes to Cyclopropenes |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201705431 https://www.ncbi.nlm.nih.gov/pubmed/28612990 https://www.proquest.com/docview/1919934606 https://www.proquest.com/docview/1909743869 |
| Volume | 56 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwELZQL-UCLRQIbZGRkFoOaRPba8fHVdRqQaIHRKUiDpFfe6G7WZHsYffUY49Vf2J_SWeSTcqCEBKc8nIcx56xvxnPg5B32nCpvVOxNTyJhRrz2HLtY2VTZazOTHCNtcWZHJ2LjxeDi5-8-Nv4EL3CDTmjma-RwY2tjh-ChqIHNppmqQTduWESRoMtREWf-_hRDIizdS_iPMYs9F3UxoQdr7--vir9BjXXkWuz9Jw-JaZrdGtx8v1oXtsjt_wlnuP__NUWebLCpXTYEtI2eRSmz8hm3qWDe06-DavFZIL5txz9WsNhPrm7uslR-7NYBk_zw2rG399d347o0PvGEIyWY8qg0KcA1AB1Lw16noWK1iXNF-6ynOFOANzYIeenJ1_yUbzKzBA7oVBhZTQIIkalljnvuOTjNDWSMcsHPvVacANTRabVgFnpwtgZAWMTAMhnRsjUMP6CbEzLaXhFqPZSQkVJQGDDjAT5KYjgvQKgBtJdiEjcjUzhVmHLMXvGZdEGXGYFdlnRd1lEDvryszZgxx9L7nUDXawYtypAfAXEJkCsi8jb_jF0Ne6jmGko51gmASmMZ1JH5GVLIP2nWAaQEVb4iLBmmP_ShmJ49uGkv3r9Ly_tksd4jvpmJvbIRv1jHvYBKNX2TcMM9ztqCk0 |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9NAEB5BOZQLLa_i0sIiIQEHt_aus2sfI9MqhTYH1EogDta-cqGJI-IckhNHjqg_sb-kM3ZsFBBCgpNle3e93uc3szPfALzMtJCZsyo0WkRhokYiNCJzoTKx0iZLtbe1tcVQDi6Sdx97rTUh-cI0_BCdwo1mRr1e0wQnhfThT9ZQcsEm2ywVkT_3bbhDYb2JPv_th45BiuPwbByMhAgpDn3L2xjxw_X86_vSb2BzHbvWm8_xFpi22o3NyZeDeWUO7PIXRsf_-q9tuLeCpqzfjKX7cMtPHsBm3kaEewif-7PFeEwhuCz7VOFlPr7-9iMnBdBi6R3LX8-m4s3196sB6ztX24KxcsQ4JjrzOCCw7KUm5zM_Y1XJ8oW9LKd0GIAPHsHF8dF5PghXwRlCmyjSWekMZRGtYsOts0KKURxrybkRPRe7LBEaV4s0Uz1upPUjqxMhex6xfKoTGWsuHsPGpJz4J8AyJyUWFHnCNlxLFKF84p1TiNVQwPMBhG3XFHbFXE4BNC6LhnOZF9RkRddkAbzq0k8bzo4_ptxre7pYzd1ZgRIsgrYEJbsAXnSvsanpKEVPfDmnNBEKYiKVWQA7zQjpPsVTRI24yQfA637-Sx2K_vDkqLvb_ZdMz2FzcH52WpyeDN8_hbv0nNTPPNmDjerr3O8jbqrMs3pm3ADg9A5p |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lj9MwEB7BIgEX3o_AAkFCAg7ZTWzXiY9VdqsujwohVlrEIfIrF7ZNRdNDe-LIEfET95cwkzSBghASnKIkY8exx_Y343kAPFGaS-VsGhnN40ikJY8MVy5KTZJqozLtbWNtMZHjY_HiZHDykxd_Gx-iV7jRzGjWa5rgc1fu_wgaSh7YZJqVxuTOfR4uCBkrSt5w8LYPIMWQO1v_Is4jSkPfhW2M2f52-e1t6TesuQ1dm71ndBV01-rW5OTj3rI2e3b9S0DH__mta3BlA0zDYctJ1-Gcn92AS3mXD-4mfBguVtMpJeCy4fsaL8vp2eevOal_VmvvwvzZYs6fn335Ng6HzjWWYGFVhgyJXntkB6x7rcn1zC_CugrzlT2t5nQUgA9uwfHo8F0-jjapGSIrUtJYaYWSiE4Tw6yzXPIySbRkzPCBS5wSXONakal0wIy0vrRacDnwiOQzLWSiGb8NO7Nq5u9CqJyUWFHsCdkwLVGA8sI7lyJSQ_HOBxB1I1PYTdxySp9xWrQRl1lBXVb0XRbA055-3kbs-CPlbjfQxWbmLgqUXxGyIS_JAB73r7Gr6SBFz3y1JJoYxTCeSRXAnZZB-k-xDDEjbvEBsGaY_9KGYjg5Ouzv7v1LoUdw8c3BqHh1NHl5Hy7TY9I9M7ELO_WnpX-AoKk2D5t58R2koA0Y |
| 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=Asymmetric+Yttrium-Catalyzed+C%28sp3%29-H+Addition+of+2-Methyl+Azaarenes+to+Cyclopropenes&rft.jtitle=Angewandte+Chemie+International+Edition&rft.au=Luo%2C+Yong&rft.au=Teng%2C+Huai-Long&rft.au=Nishiura%2C+Masayoshi&rft.au=Hou%2C+Zhaomin&rft.date=2017-07-24&rft.pub=Wiley+Subscription+Services%2C+Inc&rft.issn=1433-7851&rft.eissn=1521-3773&rft.volume=56&rft.issue=31&rft.spage=9207&rft_id=info:doi/10.1002%2Fanie.201705431&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1433-7851&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1433-7851&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1433-7851&client=summon |