Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes

Abstract

An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cis/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.