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- Title
Highly Enantioselective Construction of Strained Spiro[2,3]hexanes through a Michael Addition/Ring Expansion/Cyclization Cascade.
- Authors
Zhao, Chuan‐Gang; Feng, Zhi‐Tao; Xu, Guo‐Qiang; Gao, Ang; Chen, Jing‐Wei; Wang, Zhu‐Yin; Xu, Peng‐Fei
- Abstract
We herein report a general organocatalytic enantioselective strategy for the construction of highly strained spiro[2,3]hexane skeletons from methylenecyclopropanes and a broad selection of α,β‐unsaturated aldehydes. The reaction proceeds through a Michael addition followed by ring expansion of methylenecyclopropanes and nucleophilic attack of an enamine to realize the construction of spiro[2,3]hexanes. Key to the success of this approach are the utilization of an electron‐deficient difluoro‐substituted secondary amine catalyst and the intrinsic reactivity of methylenecyclopropanes.
- Subjects
SECONDARY amines; CONSTRUCTION; HEXANE; ALDEHYDES
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 8, p3082
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.201912834