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Rhodium‐Catalyzed Enantioselective Arylation of N ‐Substituted α,β‐Unsaturated γ‐Lactams: Preparation of Chiral 4‐Aryl‐2‐Pyrrolidones
Author(s) -
Fang JoHsuan,
Chang ChiungAn,
Gopula Balraj,
Kuo TingShen,
Wu PingYu,
Henschke Julian P.,
Wu HsyuehLiang
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600032
Subject(s) - chemistry , rhodium , enantioselective synthesis , catalysis , aryl , yield (engineering) , stereoselectivity , conjugate , diene , ligand (biochemistry) , medicinal chemistry , chiral ligand , organic chemistry , combinatorial chemistry , receptor , mathematical analysis , biochemistry , alkyl , materials science , mathematics , natural rubber , metallurgy
The preparation of chiral 4‐aryl‐2‐pyrrolidones by conjugate addition catalyzed by a rhodium(I) complex, comprising the chiral bicyclo[2.2.1] diene ligand 1 e , is reported. The reaction of various arylboronic acids and α,β‐unsaturated γ‐lactams 2 bearing various N‐ substituents proceeds in a highly stereoselective fashion (93–99.5 % ee ) even in the presence of only 0.5 mol % of the Rh catalyst affording the corresponding addition products in 31–99 % yield.
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