Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp3)−H Bonds
Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C−C bond formation between alkyl indoles and trifluoropyruvates proceeded with...
Saved in:
| Published in | Angewandte Chemie International Edition Vol. 58; no. 44; pp. 15916 - 15921 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
28.10.2019
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.201909397 |
Cover
| Abstract | Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C−C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp3−H) functionalizations of α‐azaarenes, this process does not require the use of either a strong base or an electron‐deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism.
Not just one, but two: An organocatalytic asymmetric functionalization of unactivated benzylic C(sp3)−H bonds of alkyl indoles with trifluoropyruvates was developed with high enantioselectivity. Mechanistic studies and DFT calculations show an unusual mechanism, including the first installation of a trifluoropyruvate electrophile at C3 of indoles, towards the formation of the key enamine nucleophile, followed by the addition of the second trifluoropyruvate. |
|---|---|
| AbstractList | Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp(3)-H) functionalizations of alpha-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C−C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp3−H) functionalizations of α‐azaarenes, this process does not require the use of either a strong base or an electron‐deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C−C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp3−H) functionalizations of α‐azaarenes, this process does not require the use of either a strong base or an electron‐deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. Not just one, but two: An organocatalytic asymmetric functionalization of unactivated benzylic C(sp3)−H bonds of alkyl indoles with trifluoropyruvates was developed with high enantioselectivity. Mechanistic studies and DFT calculations show an unusual mechanism, including the first installation of a trifluoropyruvate electrophile at C3 of indoles, towards the formation of the key enamine nucleophile, followed by the addition of the second trifluoropyruvate. Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C−C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp 3 −H) functionalizations of α‐azaarenes, this process does not require the use of either a strong base or an electron‐deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp3 -H) functionalizations of α-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism.Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp3 -H) functionalizations of α-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermolecular C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asymmetric C(sp -H) functionalizations of α-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. |
| Author | Ma, Dengke Chen, Min Lin, Zhenyang Sun, Jianwei Zhang, Zhihan |
| Author_xml | – sequence: 1 givenname: Dengke surname: Ma fullname: Ma, Dengke organization: The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon – sequence: 2 givenname: Zhihan surname: Zhang fullname: Zhang, Zhihan organization: The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon – sequence: 3 givenname: Min surname: Chen fullname: Chen, Min organization: The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon – sequence: 4 givenname: Zhenyang surname: Lin fullname: Lin, Zhenyang email: chzlin@ust.hk organization: The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon – sequence: 5 givenname: Jianwei orcidid: 0000-0002-2470-1077 surname: Sun fullname: Sun, Jianwei email: sunjw@ust.hk organization: The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31424147$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkstu1DAUhi1URC-wZYkisWmFMviW2FmWaEpHqtoNXbCyHPsEufLYQ5yAhifouo_YJ8HDTItUqYKVf-l8n318dA7RXogBEHpL8IxgTD_q4GBGMWlwwxrxAh2QipKSCcH2cuaMlUJWZB8dpnSTeSlx_QrtM8IpJ1wcoK9XwzcdotGj9uvRmWIedBhdTODBjO4HFGdTyCEG7d0vvQlF7IvroDdVPYItFsFGD0V7nFbs5P727rz4FINNr9HLXvsEb3bnEbo-m39pz8uLq8-L9vSiNJxgURJDNbMGiLaaVbJrmOwoEbqTuNe2MhWvmOkBc5shW4GVrMe9rDFQaKrsHqHj7b2rIX6fII1q6ZIB73WAOCVFqagaLmnDMvr-CXoTpyH_LFMMCywk4yJT73bU1C3BqtXglnpYq4ehZeDDFvgJXeyTcRAMPGIYYy5r1tR1TphkWv4_3brxz4zbOIUxq3yrmiGmNECvzK4-Dtp5RbDaLIHaLIF6XIKszZ5oD689KzS7Fp2H9T9odXq5mP91fwNmq8OC |
| CitedBy_id | crossref_primary_10_1002_anie_202201424 crossref_primary_10_1002_ejoc_202101415 crossref_primary_10_1021_acs_orglett_0c01522 crossref_primary_10_1002_adsc_202100039 crossref_primary_10_1002_adsc_202100600 crossref_primary_10_1039_D1QO00105A crossref_primary_10_1002_adsc_202401128 crossref_primary_10_1002_adsc_202301475 crossref_primary_10_1039_D1OB00048A crossref_primary_10_1016_j_mcat_2022_112648 crossref_primary_10_1021_acs_joc_4c01157 crossref_primary_10_1021_acs_orglett_9b03276 crossref_primary_10_1002_ange_202201424 crossref_primary_10_1021_acscatal_2c02164 crossref_primary_10_1021_acs_orglett_1c02676 crossref_primary_10_1002_adsc_202000448 crossref_primary_10_1021_acs_orglett_5c00008 crossref_primary_10_1016_j_checat_2024_101188 crossref_primary_10_1021_acs_orglett_3c03406 crossref_primary_10_2139_ssrn_4145115 |
| Cites_doi | 10.1002/chem.201404565 10.1002/ange.201700190 10.1021/ja206517s 10.1002/chem.201300304 10.1002/ange.201601844 10.1021/cr2003954 10.1021/cr9904009 10.1002/ange.200703317 10.1002/ange.201503549 10.1039/C7OB00413C 10.1021/ja3083494 10.1002/anie.201700190 10.1021/cr100403z 10.1038/nature10932 10.1002/anie.201503549 10.1021/ol101178u 10.1002/anie.200703317 10.1002/anie.201601844 10.1021/ar500167f 10.1007/s00214-007-0310-x 10.1002/anie.201305861 10.1021/acs.orglett.6b01831 10.1021/ja9058958 10.1021/cr900211p 10.1063/1.3382344 10.1021/cr400676v 10.1002/anie.201611306 10.1021/ol302853m 10.1002/ange.200901843 10.1038/nature08484 10.1002/ange.201305861 10.1002/ange.201611306 10.1021/jm900391x 10.1002/anie.200901843 10.1021/ja806781u 10.1039/C4CS00209A 10.1021/jacs.5b13385 10.1039/c7ob00413c 10.1021/ar700111a 10.1039/c4cs00209a |
| ContentType | Journal Article |
| Copyright | 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| Copyright_xml | – notice: 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim – notice: 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| DBID | AAYXX CITATION 17B 1KM 1KN AAWJD BLEPL DTL EGQ NPM 7TM K9. 7X8 |
| DOI | 10.1002/anie.201909397 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science - Science Citation Index Expanded - 2019 Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) PubMed Nucleic Acids Abstracts ProQuest Health & Medical Complete (Alumni) MEDLINE - Academic |
| DatabaseTitle | CrossRef Web of Science PubMed ProQuest Health & Medical Complete (Alumni) Nucleic Acids Abstracts MEDLINE - Academic |
| DatabaseTitleList | Web of Science ProQuest Health & Medical Complete (Alumni) CrossRef MEDLINE - Academic PubMed |
| 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 – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1521-3773 |
| Edition | International ed. in English |
| EndPage | 15921 |
| ExternalDocumentID | 31424147 000486396600001 10_1002_anie_201909397 ANIE201909397 |
| Genre | reviewArticle Journal Article Review |
| GrantInformation_xml | – fundername: Hong Kong RGC funderid: 16311616; 16302617; 16302318 – fundername: Shenzhen Science and Technology Innovation Committee funderid: JCYJ20160229205441091; JCYJ20170818113708560 – fundername: Shenzhen Science and Technology Innovation Committee – fundername: Hong Kong RGC; Hong Kong Research Grants Council grantid: 16302617; 16302318; 16311616 – fundername: Hong Kong RGC grantid: 16311616 – fundername: Hong Kong RGC grantid: 16302318 – fundername: Shenzhen Science and Technology Innovation Committee grantid: JCYJ20170818113708560 – fundername: Hong Kong RGC grantid: 16302617 – fundername: Shenzhen Science and Technology Innovation Committee grantid: JCYJ20160229205441091 |
| 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 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 UQL 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 AEYWJ AGHNM AGYGG CITATION 17B 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE NPM YIN 7TM K9. 7X8 |
| ID | FETCH-LOGICAL-c4107-1c2a3dce1ada358b938b217ab80fad5c5453cfe04ddced5ed83f0f860e2e952a3 |
| IEDL.DBID | DR2 |
| ISICitedReferencesCount | 21 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000486396600001 |
| ISSN | 1433-7851 1521-3773 |
| IngestDate | Thu Jul 10 17:16:08 EDT 2025 Fri Jul 25 10:35:00 EDT 2025 Wed Feb 19 02:30:37 EST 2025 Wed Jul 09 18:00:37 EDT 2025 Sat Sep 06 05:08:12 EDT 2025 Thu Apr 24 22:53:16 EDT 2025 Tue Jul 01 02:26:55 EDT 2025 Wed Jan 22 16:38:12 EST 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 44 |
| Keywords | organocatalysis NUCLEOPHILES CATALYSIS chirality DIELS-ALDER REACTIONS STRATEGY nitrogen heterocycles reaction mechanisms asymmetric catalysis ADDITIONS ACCESS |
| Language | English |
| License | 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c4107-1c2a3dce1ada358b938b217ab80fad5c5453cfe04ddced5ed83f0f860e2e952a3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
| ORCID | 0000-0002-2470-1077 0000-0003-4104-8767 0000-0001-5492-934X |
| PMID | 31424147 |
| PQID | 2307078347 |
| PQPubID | 946352 |
| PageCount | 6 |
| ParticipantIDs | wiley_primary_10_1002_anie_201909397_ANIE201909397 proquest_miscellaneous_2275948293 crossref_citationtrail_10_1002_anie_201909397 proquest_journals_2307078347 pubmed_primary_31424147 webofscience_primary_000486396600001 webofscience_primary_000486396600001CitationCount crossref_primary_10_1002_anie_201909397 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | October 28, 2019 |
| PublicationDateYYYYMMDD | 2019-10-28 |
| PublicationDate_xml | – month: 10 year: 2019 text: October 28, 2019 day: 28 |
| PublicationDecade | 2010 |
| PublicationPlace | WEINHEIM |
| PublicationPlace_xml | – name: WEINHEIM – name: Germany – name: Weinheim |
| PublicationTitle | Angewandte Chemie International Edition |
| PublicationTitleAbbrev | ANGEW CHEM INT EDIT |
| PublicationTitleAlternate | Angew Chem Int Ed Engl |
| PublicationYear | 2019 |
| Publisher | Wiley Wiley Subscription Services, Inc |
| Publisher_xml | – name: Wiley – name: Wiley Subscription Services, Inc |
| References | 2010; 12 2012; 483 2009 2009; 48 121 2010 2014; 47 2017 2017; 56 129 2009; 131 2012; 14 2016; 18 2008; 120 2014; 114 2011; 111 2011; 133 2013 2013; 52 125 2014; 20 2013; 19 2009; 52 2016 2016; 55 128 2012; 112 2012; 134 2017; 15 2015; 44 2005; 105 2007 2007; 46 119 2010; 110 2010; 132 2015 2015; 54 127 2016; 138 2009; 461 2008; 130 1990 1990; 26 26 e_1_2_6_32_1 e_1_2_6_30_2 e_1_2_6_19_3 Joule J. A. (e_1_2_6_2_2) 2010 e_1_2_6_19_2 e_1_2_6_13_2 e_1_2_6_34_1 e_1_2_6_11_2 e_1_2_6_17_2 e_1_2_6_38_2 e_1_2_6_15_2 e_1_2_6_36_2 Soloshonok V. A. (e_1_2_6_27_2) 1990; 26 e_1_2_6_20_2 e_1_2_6_41_1 e_1_2_6_7_2 e_1_2_6_9_2 e_1_2_6_28_3 e_1_2_6_3_2 e_1_2_6_5_2 e_1_2_6_1_1 e_1_2_6_24_2 e_1_2_6_49_1 e_1_2_6_22_2 e_1_2_6_20_3 e_1_2_6_28_2 e_1_2_6_43_2 e_1_2_6_45_2 e_1_2_6_24_3 e_1_2_6_26_1 e_1_2_6_47_1 e_1_2_6_31_2 e_1_2_6_18_2 e_1_2_6_35_2 e_1_2_6_10_2 e_1_2_6_12_1 e_1_2_6_31_3 e_1_2_6_33_1 e_1_2_6_16_2 e_1_2_6_39_2 e_1_2_6_14_2 e_1_2_6_37_2 e_1_2_6_42_1 e_1_2_6_21_1 (e_1_2_6_27_3) 1990; 26 e_1_2_6_40_2 e_1_2_6_8_2 e_1_2_6_8_3 e_1_2_6_4_1 e_1_2_6_6_2 e_1_2_6_48_1 e_1_2_6_23_2 e_1_2_6_48_2 e_1_2_6_29_1 e_1_2_6_44_2 e_1_2_6_25_2 e_1_2_6_46_2 Dalpozzo, R (WOS:000348922100009) 2015; 44 Meazza, M (WOS:000394998300035) 2017; 56 Meazza, M (WOS:000346056600004) 2014; 20 CHEN X (WOS:000486396600001.7) 2013; 125 Tomasi, J (WOS:000231188700004) 2005; 105 Bai, XB (WOS:000397339400045) 2017; 56 JOULE JA (WOS:000486396600001.14) 2010 Frisch, M. J. (000486396600001.11) 2009 Ogawa, S (WOS:000251228800032) 2007; 46 Takahashi, T (WOS:000266296200002) 2009; 52 BANDINI M (WOS:000486396600001.3) 2009; 121 Cacchi, S (WOS:000306031500004) 2011; 111 Xu, JF (WOS:000381236300079) 2016; 18 Shiri, M (WOS:000305108600010) 2012; 112 GRIMME S (WOS:000486396600001.12) 2010; 132 SOLOSHONOK, VA (WOS:A1990CW16800039) 1990; 26 ORI I (WOS:000486396600001.24) 2012; 483 Bandini, M (WOS:000273093700007) 2009; 48 Li, TF (WOS:000325849000013) 2013; 19 YANG W (WOS:000486396600001.33) 2016; 128 Dengke (000486396600001.41) 2019 Zhuo, CX (WOS:000340702000032) 2014; 47 Best, D (WOS:000310720900011) 2012; 134 Lancianesi, S (WOS:000339471700006) 2014; 114 ZHOU L (WOS:000486396600001.36) 2015; 127 Zuend, SJ (WOS:000270817700044) 2009; 461 Zhou, LJ (WOS:000358501500041) 2015; 54 Liu, YK (WOS:000295604400060) 2011; 133 SOLOSHONOK VA (WOS:000486396600001.27) 1990; 26 Zuend, SJ (WOS:000271272000057) 2009; 131 Trost, BM (WOS:000260301700036) 2008; 130 Chen, JB (WOS:000400868000002) 2017; 15 Cid, MB (WOS:000280799100005) 2010; 12 MEAZZA M (WOS:000486396600001.21) 2017; 129 Chen, XK (WOS:000328812600038) 2013; 52 Zhao, Y (WOS:000253323800001) 2008; 41 Kochanowska-Karamyan, AJ (WOS:000280985800001) 2010; 110 Izquierdo, J (WOS:000372477700006) 2016; 138 Yang, W (WOS:000377921400029) 2016; 55 Xiao, YC (WOS:000311926000033) 2012; 14 OGAWA S (WOS:000486396600001.22) 2007; 119 |
| References_xml | – volume: 105 start-page: 2999 year: 2005 end-page: 3093 publication-title: Chem. Rev. – volume: 138 start-page: 3282 year: 2016 end-page: 3285 publication-title: J. Am. Chem. Soc. – volume: 26 26 start-page: 358 419 year: 1990 1990 end-page: 363 425 publication-title: J. Org. Chem. USSR (Engl. Transl.) Zh. Org. Khim. – volume: 18 start-page: 3822 year: 2016 end-page: 3825 publication-title: Org. Lett. – volume: 112 start-page: 3508 year: 2012 end-page: 3549 publication-title: Chem. Rev. – volume: 134 start-page: 18193 year: 2012 end-page: 18196 publication-title: J. Am. Chem. Soc. – volume: 133 start-page: 15212 year: 2011 end-page: 15218 publication-title: J. Am. Chem. Soc. – volume: 46 119 start-page: 8666 8820 year: 2007 2007 end-page: 8669 8823 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 14 start-page: 5940 year: 2012 end-page: 5943 publication-title: Org. Lett. – volume: 52 start-page: 3142 year: 2009 end-page: 3145 publication-title: J. Med. Chem. – volume: 132 start-page: 154104 year: 2010 end-page: 154119 publication-title: J. Chem. Phys. – volume: 483 start-page: 315 year: 2012 end-page: 319 publication-title: Nature – volume: 55 128 start-page: 6954 7068 year: 2016 2016 end-page: 6958 7072 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 19 start-page: 9147 year: 2013 end-page: 9150 publication-title: Chem. Eur. J. – volume: 111 start-page: 215 year: 2011 end-page: 283 publication-title: Chem. Rev. – year: 2010 – volume: 15 start-page: 3550 year: 2017 end-page: 3567 publication-title: Org. Biomol. Chem. – volume: 461 start-page: 968 year: 2009 end-page: 970 publication-title: Nature – volume: 110 start-page: 4489 year: 2010 end-page: 4497 publication-title: Chem. Rev. – volume: 56 129 start-page: 3684 3738 year: 2017 2017 end-page: 3688 3742 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 120 start-page: 215 year: 2008 end-page: 241 publication-title: Theor. Chem. Acc. – volume: 114 start-page: 7108 year: 2014 end-page: 7149 publication-title: Chem. Rev. – volume: 52 125 start-page: 11134 11340 year: 2013 2013 end-page: 11137 11343 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 131 start-page: 15358 year: 2009 end-page: 15374 publication-title: J. Am. Chem. Soc. – volume: 47 start-page: 2558 year: 2014 end-page: 2573 publication-title: Acc. Chem. Res. – volume: 48 121 start-page: 9608 9786 year: 2009 2009 end-page: 9644 9824 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 130 start-page: 14092 year: 2008 end-page: 14093 publication-title: J. Am. Chem. Soc. – volume: 54 127 start-page: 9092 9220 year: 2015 2015 end-page: 9096 9224 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 44 start-page: 742 year: 2015 end-page: 778 publication-title: Chem. Soc. Rev. – volume: 56 129 start-page: 1634 1656 year: 2017 2017 end-page: 1638 1660 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 12 start-page: 3586 year: 2010 end-page: 3589 publication-title: Org. Lett. – volume: 20 start-page: 16853 year: 2014 end-page: 16857 publication-title: Chem. Eur. J. – ident: e_1_2_6_17_2 doi: 10.1002/chem.201404565 – volume: 26 start-page: 358 year: 1990 ident: e_1_2_6_27_2 publication-title: J. Org. Chem. USSR (Engl. Transl.) – ident: e_1_2_6_20_3 doi: 10.1002/ange.201700190 – ident: e_1_2_6_29_1 – ident: e_1_2_6_22_2 doi: 10.1021/ja206517s – ident: e_1_2_6_16_2 doi: 10.1002/chem.201300304 – ident: e_1_2_6_48_2 doi: 10.1002/ange.201601844 – ident: e_1_2_6_10_2 doi: 10.1021/cr2003954 – ident: e_1_2_6_35_2 – ident: e_1_2_6_44_2 doi: 10.1021/cr9904009 – ident: e_1_2_6_4_1 – ident: e_1_2_6_31_3 doi: 10.1002/ange.200703317 – ident: e_1_2_6_28_3 doi: 10.1002/ange.201503549 – ident: e_1_2_6_47_1 – ident: e_1_2_6_7_2 doi: 10.1039/C7OB00413C – ident: e_1_2_6_15_2 doi: 10.1021/ja3083494 – ident: e_1_2_6_20_2 doi: 10.1002/anie.201700190 – ident: e_1_2_6_9_2 doi: 10.1021/cr100403z – ident: e_1_2_6_38_2 doi: 10.1038/nature10932 – ident: e_1_2_6_28_2 doi: 10.1002/anie.201503549 – ident: e_1_2_6_14_2 doi: 10.1021/ol101178u – ident: e_1_2_6_31_2 doi: 10.1002/anie.200703317 – ident: e_1_2_6_48_1 doi: 10.1002/anie.201601844 – ident: e_1_2_6_5_2 doi: 10.1021/ar500167f – ident: e_1_2_6_39_2 – ident: e_1_2_6_43_2 doi: 10.1007/s00214-007-0310-x – ident: e_1_2_6_24_2 doi: 10.1002/anie.201305861 – ident: e_1_2_6_25_2 doi: 10.1021/acs.orglett.6b01831 – ident: e_1_2_6_33_1 doi: 10.1021/ja9058958 – ident: e_1_2_6_36_2 – ident: e_1_2_6_12_1 – ident: e_1_2_6_3_2 doi: 10.1021/cr900211p – ident: e_1_2_6_45_2 doi: 10.1063/1.3382344 – ident: e_1_2_6_11_2 doi: 10.1021/cr400676v – ident: e_1_2_6_26_1 – ident: e_1_2_6_19_2 doi: 10.1002/anie.201611306 – ident: e_1_2_6_34_1 – ident: e_1_2_6_1_1 – ident: e_1_2_6_42_1 – ident: e_1_2_6_23_2 doi: 10.1021/ol302853m – ident: e_1_2_6_46_2 – ident: e_1_2_6_8_3 doi: 10.1002/ange.200901843 – ident: e_1_2_6_32_1 doi: 10.1038/nature08484 – ident: e_1_2_6_24_3 doi: 10.1002/ange.201305861 – ident: e_1_2_6_41_1 – ident: e_1_2_6_19_3 doi: 10.1002/ange.201611306 – ident: e_1_2_6_30_2 doi: 10.1021/jm900391x – volume-title: Heterocyclic Chemistry year: 2010 ident: e_1_2_6_2_2 – ident: e_1_2_6_40_2 – ident: e_1_2_6_21_1 – ident: e_1_2_6_37_2 – ident: e_1_2_6_8_2 doi: 10.1002/anie.200901843 – volume: 26 start-page: 419 year: 1990 ident: e_1_2_6_27_3 publication-title: Zh. Org. Khim. – ident: e_1_2_6_13_2 doi: 10.1021/ja806781u – ident: e_1_2_6_6_2 doi: 10.1039/C4CS00209A – ident: e_1_2_6_18_2 doi: 10.1021/jacs.5b13385 – ident: e_1_2_6_49_1 – year: 2009 ident: 000486396600001.11 publication-title: Gaussian 2009 – volume: 56 start-page: 3684 year: 2017 ident: WOS:000397339400045 article-title: Catalytic Enantioselective γ-Selective Additions of 2-Allylazaarenes to Activated Ketones publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201700190 – volume: 133 start-page: 15212 year: 2011 ident: WOS:000295604400060 article-title: Asymmetric Catalysis of Diels-Alder Reactions with in Situ Generated Heterocyclic ortho-Quinodimethanes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja206517s – volume: 15 start-page: 3550 year: 2017 ident: WOS:000400868000002 article-title: Recent progress in transition-metal-catalyzed enantioselective indole functionalizations publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c7ob00413c – volume: 52 start-page: 3142 year: 2009 ident: WOS:000266296200002 article-title: Synthesis and Evaluation of a Novel Indoledione Class of Long Chain Fatty Acid Elongase 6 (ELOVL6) Inhibitors publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm900391x – volume: 47 start-page: 2558 year: 2014 ident: WOS:000340702000032 article-title: Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar500167f – volume: 138 start-page: 3282 year: 2016 ident: WOS:000372477700006 article-title: Base-Catalyzed Asymmetric α-Functionalization of 2-(Cyanomethyl)azaarene N-Oxides Leading to Quaternary Stereocenters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b13385 – volume: 125 start-page: 11340 year: 2013 ident: WOS:000486396600001.7 publication-title: ANGEW CHEM – volume: 110 start-page: 4489 year: 2010 ident: WOS:000280985800001 article-title: Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety publication-title: CHEMICAL REVIEWS doi: 10.1021/cr900211p – volume: 127 start-page: 9220 year: 2015 ident: WOS:000486396600001.36 publication-title: ANGEW CHEM – volume: 131 start-page: 15358 year: 2009 ident: WOS:000271272000057 article-title: Mechanism of Amido-Thiourea Catalyzed Enantioselective Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent Interactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja9058958 – volume: 19 start-page: 9147 year: 2013 ident: WOS:000325849000013 article-title: A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201300304 – volume: 12 start-page: 3586 year: 2010 ident: WOS:000280799100005 article-title: Nitrophenylacetonitriles as Versatile Nucleophiles in Enantioselective Organocatalytic Conjugate Additions publication-title: ORGANIC LETTERS doi: 10.1021/ol101178u – volume: 26 start-page: 419 year: 1990 ident: WOS:A1990CW16800039 article-title: REACTIONS OF METHYLTRIFLUOROPYRUVATE AND ITS N-METHOXYCARBONYLIMINE WITH PI-ENRICHED HETEROCYCLES AND DIPOLAR COMPOUNDS publication-title: ZHURNAL ORGANICHESKOI KHIMII – volume: 52 start-page: 11134 year: 2013 ident: WOS:000328812600038 article-title: Functionalization of Benzylic C(sp3)-H Bonds of Heteroaryl Aldehydes through N-Heterocyclic Carbene Organocatalysis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201305861 – volume: 41 start-page: 157 year: 2008 ident: WOS:000253323800001 article-title: Density functionals with broad applicability in chemistry publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar700111a – year: 2010 ident: WOS:000486396600001.14 publication-title: HETEROCYCLIC CHEM – volume: 55 start-page: 6954 year: 2016 ident: WOS:000377921400029 article-title: Enantioselective Oxetane Ring Opening with Chloride: Unusual Use of Wet Molecular Sieves for the Controlled Release of HCl publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201601844 – volume: 48 start-page: 9608 year: 2009 ident: WOS:000273093700007 article-title: Catalytic Functionalization of Indoles in a New Dimension publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200901843 – volume: 56 start-page: 1634 year: 2017 ident: WOS:000394998300035 article-title: Synergistic Diastereo- and Enantioselective Functionalization of Unactivated Alkyl Quinolines with ,-Unsaturated Aldehydes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201611306 – volume: 14 start-page: 5940 year: 2012 ident: WOS:000311926000033 article-title: Asymmetric Diels-Alder Reaction of 2-Methyl-3-indolylmethanols via in Situ Generation of o-Quinodimethanes publication-title: ORGANIC LETTERS doi: 10.1021/ol302853m – year: 2019 ident: 000486396600001.41 publication-title: Angew.Chem.,Int.Ed – volume: 134 start-page: 18193 year: 2012 ident: WOS:000310720900011 article-title: Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja3083494 – volume: 44 start-page: 742 year: 2015 ident: WOS:000348922100009 article-title: Strategies for the asymmetric functionalization of indoles: an update publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c4cs00209a – volume: 26 start-page: 358 year: 1990 ident: WOS:000486396600001.27 publication-title: J ORG CHEM USSR – volume: 132 year: 2010 ident: WOS:000486396600001.12 publication-title: J CHEM PHYS – volume: 18 start-page: 3822 year: 2016 ident: WOS:000381236300079 article-title: N-Heterocyclic Carbene Catalyzed [4+2] Annulation Reactions with in Situ Generated Heterocyclic ortho-Quinodimethanes publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.6b01831 – volume: 128 start-page: 7068 year: 2016 ident: WOS:000486396600001.33 publication-title: ANGEW CHEM – volume: 111 start-page: PR215 year: 2011 ident: WOS:000306031500004 article-title: Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100403z – volume: 461 start-page: 968 year: 2009 ident: WOS:000270817700044 article-title: Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids publication-title: NATURE doi: 10.1038/nature08484 – volume: 114 start-page: 7108 year: 2014 ident: WOS:000339471700006 article-title: Synthetic Approaches to 3-(2-Nitroalkyl) Indoles and Their Use to Access Tryptamines and Related Bioactive Compounds publication-title: CHEMICAL REVIEWS doi: 10.1021/cr400676v – volume: 129 start-page: 1656 year: 2017 ident: WOS:000486396600001.21 publication-title: ANGEW CHEM – volume: 105 start-page: 2999 year: 2005 ident: WOS:000231188700004 article-title: Quantum mechanical continuum solvation models publication-title: CHEMICAL REVIEWS doi: 10.1021/cr9904009 – volume: 130 start-page: 14092 year: 2008 ident: WOS:000260301700036 article-title: Strategy for Employing Unstabilized Nucleophiles in Palladium-Catalyzed Asymmetric Allylic Alkylations publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja806781u – volume: 20 start-page: 16853 year: 2014 ident: WOS:000346056600004 article-title: Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201404565 – volume: 483 start-page: 315 year: 2012 ident: WOS:000486396600001.24 publication-title: NATURE – volume: 112 start-page: 3508 year: 2012 ident: WOS:000305108600010 article-title: Indoles in Multicomponent Processes (MCPs) publication-title: CHEMICAL REVIEWS doi: 10.1021/cr2003954 – volume: 119 start-page: 8820 year: 2007 ident: WOS:000486396600001.22 publication-title: ANGEW CHEM – volume: 46 start-page: 8666 year: 2007 ident: WOS:000251228800032 article-title: Cinchona-alkaloid-catalyzed enantioselective direct aldol-type reaction of oxindoles with ethyl trifluoropyruvate publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200703317 – volume: 121 start-page: 9786 year: 2009 ident: WOS:000486396600001.3 publication-title: ANGEW CHEM doi: 10.1002/ange.200901843 – volume: 54 start-page: 9092 year: 2015 ident: WOS:000358501500041 article-title: Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201503549 |
| SSID | ssj0028806 |
| Score | 2.4184937 |
| SecondaryResourceType | review_article |
| Snippet | Described here is a direct catalytic asymmetric functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref wiley |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 15916 |
| SubjectTerms | asymmetric catalysis Asymmetry Catalysts Chemistry Chemistry, Multidisciplinary chirality Enantiomers Indoles nitrogen heterocycles organocatalysis Phosphoric acid Physical Sciences reaction mechanisms Science & Technology Substrates Urea |
| Title | Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp3)−H Bonds |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201909397 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000486396600001 https://www.ncbi.nlm.nih.gov/pubmed/31424147 https://www.proquest.com/docview/2307078347 https://www.proquest.com/docview/2275948293 |
| Volume | 58 |
| WOS | 000486396600001 |
| WOSCitedRecordID | wos000486396600001 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwEB6hcoAL70egVEaqBBzSJraTTY7b7a62SPSAWKmcIj8lBEoqsosEv4AzP5FfwozzoFuEQHDLyuONbI8znx_fNwD7Exxzp1waF1kpY-nyIta51bHTXnNV-onyxEZ-dZovV_LlWXZ2gcXf6UOMG240M8L3mia40u3hT9FQYmDT1awS1-Ql0clTkZN4_vHrUT-Ko3N29CIhYspCP6g2Jvxwu_p2VPoFal6KSttANkSixU1QQxu6CyjvDzZrfWC-XJJ3_J9G3oIbPUxl086vbsMVV9-Ba7MhO9xdeBtInE3Y_fmMRmxON2reNW3Iq4OfULbAiNltNPZUT9Z4tqqJSPEJAa5lJzWpSbHZ8_ZcvPj-9duSUY7j9h6sFvM3s2Xcp2mIjUxJYtJwJaxxqbJKZIUuRaFxoaN0kXhlM4MYTRjvEmnRyGbOFsInvsgTx12ZYd37sFM3tXsILMXVk9eIQQzCNCFlqUtr6R-F0Yk2MoJ4GKbK9BrmlErjQ9WpL_OKOqwaOyyCZ6P9eafe8VvL3WHUq34WtxVdkqdjTonFT8di7Gg6VFG1azZowyekeIOoKYIHnbeMrxJEI0yp9v5F9xnLA6MfIWKeh0OWCNK_MZv1DSfRgnUEPPjPH5pXTU9P5uOvR_9S6TFcp2eK27zYhZ31x417goBsrffg6vTo-GixFybfDzxLLxU |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lj9MwEB7BclguvB-BBYy0EnDIbmI7aXJclVYt7PaAthKcIj8lBEpWtEWCX8CZn8gvYcZ5QBchEBwTjxPZHns-2zPfAOyPcMydcmlcZKWMpcuLWOdWx057zVXpR8pTNPLJIp8t5YvXWe9NSLEwLT_EcOBGMyOs1zTB6UD68AdrKIVgk29WiZvycnQRLklEG7T_ev5qYJDiqJ5tgJEQMeWh73kbE364XX_bLv0CNs_ZpW0oG2zR9CrovhWtC8q7g81aH5jP5wge_6uZ1-BKh1TZUata1-GCq2_A7rhPEHcT3oQ4ziYcAH1CITYhp5q3zSqk1sFVlE3RaLZnjV20J2s8W9YUS_ERMa5l85oIpdj46epMPPv25euMUZrj1S1YTien41ncZWqIjUyJZdJwJaxxqbJKZIUuRaFxr6N0kXhlM4MwTRjvEmlRyGbOFsInvsgTx12ZYd3bsFM3tbsLLMUNlNcIQwwiNSFlqUtr6YvC6EQbGUHcj1NlOhpzyqbxvmoJmHlFHVYNHRbBk0H-rCXw-K3kXj_sVTeRVxX5ydNNp8Tix0MxdjTdq6jaNRuU4SMivUHgFMGdVl2GXwmKJEyp9v7P-jOUh6B-RIl5Hu5ZIkj_RmzcNZx4C9YR8KBAf2hedbSYT4ane_9S6RHszk5Pjqvj-eLlfbhM78mM82IPdtYfNu4B4rO1fhhm4HeckzHC |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3bbtNAEB1BkaAv5V4MBYxUCXhwa--uHfuxCokSLhFCRCpP1l4l1MqOSFIJvoBnPpEvYWZ9oSlCIHh0djbW7s56zl7OGYD9AY65lTaJ8rQQkbBZHqnMqMgqp5gs3EA6YiO_mWWTuXh5nB6fY_E3-hD9hhvNDP-9pgm-MO7wp2goMbDpalaBa_JicBmuiAzhBMGid72AFEPvbPhFnEeUhr6TbYzZ4Wb9zbD0C9a8EJY2kawPRePrILtGNDdQTg7WK3Wgv1zQd_yfVt6AnRanhkeNY92ES7a6BdeGXXq42_DBszhrv_3zGY3CEV2p-VgvfWId_IaGYwyZzU5jy_UMaxfOK2JSnCHCNeG0IjmpcPhsueDPv3_9NgkpyfHyDszHo_fDSdTmaYi0SEhjUjPJjbaJNJKnuSp4rnClI1UeO2lSjSCNa2djYdDIpNbk3MUuz2LLbJFi3buwVdWVvQdhgssnpxCEaMRpXIhCFcbQP3KtYqVFAFE3TKVuRcwpl8Zp2cgvs5I6rOw7LICnvf2ike_4reVeN-plO42XJd2Sp3NOgcVP-mLsaDpVkZWt12jDBiR5g7ApgN3GW_pXceIRJlR7_7z79OWe0o8YMcv8KUsAyd-YDduGk2rBKgDm_ecPzSuPZtNR_3T_Xyo9hqtvX4zL19PZqwewTT9TDGf5HmytPq3tQwRnK_XIz78f2mkwcQ |
| 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=Organocatalytic+Enantioselective+Functionalization+of+Unactivated+Indole+C%28sp3%29-H+Bonds&rft.jtitle=Angewandte+Chemie+International+Edition&rft.au=Ma%2C+Dengke&rft.au=Zhang%2C+Zhihan&rft.au=Chen%2C+Min&rft.au=Lin%2C+Zhenyang&rft.date=2019-10-28&rft.pub=Wiley&rft.eissn=1521-3773&rft.volume=58&rft.issue=44&rft.spage=15916&rft.epage=15921&rft_id=info:doi/10.1002%2Fanie.201909397&rft_id=info%3Apmid%2F31424147&rft.externalDBID=n%2Fa&rft.externalDocID=000486396600001 |
| 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 |