Epoxysilane Rearrangement Induced by a Carbanion Generated by Conjugate Addition of Enolates of Chloroacetate and α-Chloroacetamides: Formation of Functionalized Cyclopropane Derivatives

Reaction of an enoate bearing an epoxysilane moiety at the α-position with lithium enolate of 2-chloroacetamide afforded highly functionalized cyclopropane derivatives via a tandem process that involves Michael addition, ring opening of the epoxide, Brook rearrangement, and intramolecular alkylation.