alpha -AMINO ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS. A GENERAL SYNTHESIS OF D- alpha -AMINO ACIDS FROM L-SERINE.

Article abstract of DOI:10.1021/ja00316a047

A short and chirally efficient synthesis of four D- alpha -amino acids is described with L-serine as the chiral educt. The key C-C bond-forming reactions are the aminoacylations of organometallics with the lithium salt of N-(phenylsulfonyl)-L-serine (2) to give optically pure N-blocked alpha -amino ketones. Reduction of the carbonyl group to carbinol or methylene followed by oxidation of the hydroxymethyl to carboxyl gives the N-blocked D-amino acids. The examples investigated (norleucine, alpha -aminopimelic acid, DOPA, and allothreonine) demonstrate the broad applicability of the method.