Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β‐Unsaturated γ‐Butyrolactams to Dienones |
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| Authors: | Xiaodong Gu Tingting Guo Yuanyuan Dai Allegra Franchino Jie Fei Chuncheng Zou Prof. Dr. Darren J. Dixon Prof. Dr. Jinxing Ye |
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| Affiliation: | 1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China);2. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK) |
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| 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. |
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| Keywords: | asymmetric catalysis conjugation cyclizations nucleophilic addition organocatalysis |
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