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Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β‐Unsaturated γ‐Butyrolactams to Dienones
Author(s) -
Gu Xiaodong,
Guo Tingting,
Dai Yuanyuan,
Franchino Allegra,
Fei Jie,
Zou Chuncheng,
Dixon Darren J.,
Ye Jinxing
Publication year - 2015
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.201504276
Subject(s) - stereocenter , michael reaction , isomerization , steric effects , chemistry , stereochemistry , catalysis , enantioselective synthesis , organic chemistry
Abstract An asymmetric doubly vinylogous Michael addition (DVMA) of α,β‐unsaturated γ‐butyrolactams to sterically congested β‐substituted cyclic dienones with high site‐, diastereo‐, and enantioselectivity has been achieved. An unprecedented DVMA/vinylogous Michael addition/isomerization cascade reaction affords chiral fused tricyclic γ‐lactams with four newly formed stereocenters.