Enantioselective Allylation of <i>β</i><i>,</i><i>γ</i>-Unsaturated Aldehydes Generated via Lewis Acid Induced Rearrangement of 2-Vinyloxiranes

Abstract

[reaction: see text] 2-Vinyloxiranes have been found to be excellent surrogates to beta,gamma-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)(3), are effectively trapped by the chiral allylating agents based on alpha-pinene, affording bishomoallylic alcohols in high yield and excellent selectivity.