Preparation of a novel, camphor-derived sulfide and its evaluation as a chiral auxiliary mediator in asymmetric epoxidation via the Corey–Chaykovsky reaction

Abstract

Sulfonium ylide-mediated asymmetric one-pot synthesis of optically active epoxides from aldehydes and bromides via the Corey–Chaykovsky reaction is described. The optically pure chiral sulfide was readily prepared from natural camphor via thiabutadiene Diels–Alder cycloaddition, followed by LiAlH4 reduction and hydrogenation of the cycloadduct.