Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives.

Abstract

We have developed an efficient method for the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives based on highly enantio- and diastereoselective aldol reactions of the silicon enolate derived from N-trifluoroacetylglycinate with aldehydes using a chiral zirconium catalyst. The resulting N-trifluoroacetyl group is easily cleaved under either acidic or basic conditions and can be used directly as a protecting group for further transformations.