ChemInform Abstract: Attempt to Rationalize the Diastereoselectivity in the Addition of Ester Enolate to Optically Active α,β-Epoxyaldehydes

Aldol condensations on α,β-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and syn γ,δ-epoxy β-hydroxyesters and their NMR and IR spectrostroscopic properties.