A new diastereoselective approach to the synthesis of α-hydroxy- β-amino acids based on the frame of captodative olefins

Abstract

A new diasteroselective approach for the preparation of chiral α-hydroxy-β-amino acids is described. It is based on the conjugate addition of either (R)-(+)-methylbenzylamine (4) or its lithium salt to the captodative olefins: methyl 2-aroyloxy- and 2-methacryloxy acrylates, 1a-1b and 1c. The highest diastereoselectivity is obtained when the addition is carried out with the chiral lithium amide in the presence of trialkylsilyl chlorides. ©ARKAT.