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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-aroyloxyand 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.

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