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Palladium‐Catalyzed Asymmetric Intramolecular Reductive Heck Desymmetrization of Cyclopentenes: Access to Chiral Bicyclo[3.2.1]octanes
Author(s) -
Yuan Zhenbo,
Feng Ziwen,
Zeng Yuye,
Zhao Xiaobin,
Lin Aijun,
Yao Hequan
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201900059
Subject(s) - desymmetrization , bicyclic molecule , palladium , stereocenter , chemistry , intramolecular force , heck reaction , catalysis , enantioselective synthesis , organic chemistry , combinatorial chemistry , medicinal chemistry
A palladium‐catalyzed asymmetric reductive Heck reaction of unactivated aliphatic alkenes, with eliminable β‐hydrogen atoms, has been realized for the first time. A series of optically active bicyclo[3.2.1]octanes bearing chiral quaternary and tertiary carbon stereocenters were obtained in good yields with excellent enantioselectivities, exhibiting good functional‐group tolerance and scalability. Moreover, deuterated optically active bicyclo[3.2.1]octanes were also obtained in high efficiency.