Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of alpha,beta-Unsaturated gamma-Butyrolactams to Dienones

作者:Gu, Xiaodong; Guo, Tingting; Dai, Yuanyuan; Franchino, Allegra; Fei, Jie; Zou, Chuncheng; Dixon, Darren J.*; Ye, Jinxing
来源:Angewandte Chemie - International Edition, 2015, 54(35): 10249-10253.
DOI:10.1002/anie.201504276

摘要

An asymmetric doubly vinylogous Michael addition (DVMA) of alpha,beta-unsaturated gamma-butyrolactams to sterically congested beta-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 gamma-lactams with four newly formed stereocenters.