Catalytic Enantioselective Desymmetrization of COT-Monoepoxide. Maximum Deviation from Coplanarity for an SN2’-Cuprate Alkylation,

Abstract

The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction−isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the π-orbital of the double bond and the σ-bond connecting the leaving group ever observed for an SN2‘-cuprate alkylation