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

Xiaodong Gu,Tingting Guo,Yuanyuan Dai,Allegra Franchino,Jie Fei,Chuncheng Zou,Darren J. Dixon,Jinxing Ye

Angewandte Chemie（2015）

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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.

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关键词

asymmetric catalysis,conjugation,cyclizations,nucleophilic addition,organocatalysis

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