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

Abstract

Optically active <i>cis</i>-cyclopropane carboxylates are prepared via the Rh₂(<i>S</i>-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