β, β-Difluoro analogs of α-oxo-β-phenylpropionic acid and phenylalanine

M Schlosser, N Brügger, W Schmidt, N Amrhein

Index: Schlosser, Manfred; Bruegger, Nadia; Schmidt, Werner; Amrhein, Nikolaus Tetrahedron, 2004 , vol. 60, # 35 p. 7731 - 7742

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Citation Number: 26

Abstract

A simple three-step procedure converted the readily accessible (2-bromo-1, 1-difluoroethyl) arenes () into α-aryl-α, α-difluoroacetaldehydes (). Subsequent hydrocyanation, hydrolysis, oxidation and again hydrolysis afforded β-aryl-β, β-difluoro-α-oxopropionic acids (). Reductive amination transformed the oxoacids into a separable mixture of α-hydroxyacids and racemic β, β-difluoro-β-phenylalanine derivatives (). Enantiomerically pure β, β- ...