Highly Enantioselective Construction of Strained Spiro[2,3]hexanes through a Michael Addition/Ring Expansion/Cyclization Cascade.,Angewandte Chemie International Edition

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Highly Enantioselective Construction of Strained Spiro[2,3]hexanes through a Michael Addition/Ring Expansion/Cyclization Cascade.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-21 , DOI: 10.1002/anie.201912834
Chuan-Gang Zhao ₁ , Zhi-Tao Feng ₂ , Guo-Qiang Xu ₁ , Ang Gao ₁ , Jing-Wei Chen ₁ , Zhu-Yin Wang ₁ , Peng-Fei Xu ₁

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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.

中文翻译：

通过迈克尔加成/环扩环/环化级联反应，对螺[2,3]正己烷进行高度对映选择性的构建。

我们在此报告了一种通用的有机催化对映选择性策略，该策略可用于从亚甲基环丙烷构建高应变比螺[2,3]己烷骨架，并提供多种α，β-不饱和醛。该反应通过迈克尔加成进行，随后亚甲基环丙烷的扩环和烯胺的亲核攻击以实现螺[2,3]己烷的构建。该方法成功的关键是利用电子不足的二氟取代的仲胺催化剂和亚甲基环丙烷的固有反应性。

更新日期：2020-01-22

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