Stereoselective reactions of α,β-epoxy-aldehydes; the formation of "chelation controlled" products

Article abstract of DOI:10.1016/S0040-4039(00)92086-0

Treatment of the α,β-epoxy-aldehydes (l) and (2) with Lewis acids followed by in situ reaction with carbon nucleophiles produces halohydrins of the products of "chelation controlled" addition to the aldehyde with high diastereoselectivity; The regiochemistry of epoxide opening is determined by choice of Lewis acid.