Efficient resolution of rac-2-cyano-2-methyl-3-phenylpropanoic acid. An appropriate starting material for the enantioconvergent synthesis of (S)-α-methylphenylalanine …

R Badorrey, C Cativiela, MD Dı́az-de-Villegas…

Index: Badorrey, Ramon; Cativiela, Carlos; Diaz-de-Villegas, Maria D.; Galvez, Jose A. Tetrahedron Asymmetry, 2003 ,  vol. 14,  # 15  p. 2201 - 2207

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Citation Number: 8

Abstract

A large laboratory scale synthesis of (S)-α-methylphenylalanine from benzaldehyde and methyl cyanoacetate has been developed. The synthesis is based on the following sequence:(i) preparation of racemic 2-cyano-2-methyl-3-phenylpropanoic acid,(ii) resolution of the enantiomers by crystallisation using norephedrine, and (iii) development of an efficient enantioconvergent synthesis of (S)-α-methylphenylalanine from enantiopure (S)-and (R)-2 ...