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Enantioselective Rhodium‐Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts
Author(s) -
Wang Yan,
Liu Yunlong,
Zhang Dongdong,
Wei Hao,
Shi Min,
Wang Feijun
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511663
Subject(s) - enantioselective synthesis , rhodium , quinoline , catalysis , chemistry , combinatorial chemistry , organic chemistry
A highly enantioselective rhodium(I)‐catalyzed dearomative arylation or alkenylation of easily available N‐alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99 % ee . This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asymmetric synthesis of bioactive tetrahydroquinoline and the total syntheses of (−)‐angustureine and (+)‐cuspareine.