Asymmetric synthesis of (4 S,5 S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid using a 1,2-addition of PhMgBr to an N-sulfinimine derived from ( R)-glyceraldehyde acetonide and ( S)- t-BSA

Abstract

We report an asymmetric synthesis of (4 S,5 S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid via stereoselective addition of phenylmagnesium bromide (PhMgBr) to an N-sulfinimine derived from ( R)-glyceraldehyde acetonide. ( S)- and ( R)-Glyceraldehyde acetonides, important chiral synthons in synthetic organic chemistry, are prepared from the corresponding epichlorohydrin using an identical synthetic methodology.