Preparation of Optically Active cis -Cyclopropane Carboxylates: Cyclopropanation of α-Silyl Stryenes with Aryldiazoacetates and Desilylation of the Resulting Silyl Cyclopropanes

作者：Yan Su, Qingfang Li, Yu‐Ming Zhao, Peiming Gu · 发表于：Organic Letters · 年份：2016 · DOI：10.1021/acs.orglett.6b02117 · 被引用次数：29 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic Alkyne Reactions、Catalytic C–H Functionalization Methods

Optically active cis-cyclopropane carboxylates are prepared via the Rh2(S-PTAD)4-catalyzed cyclopropanation of α-silyl styrenes with aryl diazoacetates followed by desilylation of the resulting silyl cyclopropane carboxylates. The conjugation of the aryl ring with C═C bond and π stacking are proposed for the stereoselectivity of cyclopropanation, and configuration inversion is observed with the desilylation process.