Asymmetric Synthesis of β-Amino-α, α-dimethyl-β-phenylpropionic Acid. The Reactions of Chiral Schiff Bases with Dimethylketene and with Reformatsky Reagent

Abstract

Asymmetric synthesis of optically active β-amino-α, α-dimethyl-β-phenylpropionic acid (7) was achieved by the reaction of chiral Schiff bases with dimethylketene or with Reformatsky reagent, in the range of 33-35% optical purities. The specific rotation and configuration of 7 were determined by correlation with authentic R (+)-β-benzoylamino-α, α-dimethyl-β-phenylethanol. The steric courses of these reactions are discussed.