Stereoselective synthesis of α-substituted serines from protected erythrulose oximes

Abstract

The additions of organolithium reagents to the CN bond of several chiral oxime ethers derived from erythrulose afforded protected amino polyols with high diastereoselectivity. Four of the latter compounds have been converted into the α,α-disubstituted α-amino acids ( R)-2-(−)-methylserine, ( S)-2-(+)-methylserine, ( R)-(+)-2-phenylserine and ( R)-(−)-2- n-butylserine.