Diastereoselective Addition of Nucleophiles to Carbonyl Compounds and Imines Controlled by α, β-Epoxy Group and Its Application in Organic Synthesis

Abstract

Diastereoselective addition of nucleophiles to carbonyl and imine compounds with α- and/or β-substituents has been a valuable tool in the synthesis of complex molecules. Since optically active epoxides are easily accessible by Sharpless asymmetric epoxidation, the utiltiy of this group as a stereocontrolling element in such reactions is getting more and more highlighted recently. This account surveys diastereoselectivities in the nucleophilic additions to the C = X bonds found in i) α, β-epoxy aldehydes, ii) α, β-epoxy ketones, iii) α, β-epoxy imines, and iv) γ, δ-epoxy-α, β-unsaturated carbonyl compounds (conjugate addition) in this order and also presents some devices to achieve high selectivities as well as possible rationale of the stereochemical outcome in certain cases. Application of these reactions to the synthesis of biologically active compounds is also illustrated.