Tetrahedron

An efficient and stereodivergent synthesis of threo-and erythro-β-methylphenylalanine. Resolution of each racemic pair by semipreparative HPLC

M Alı́as, MP López, C Cativiela

Index: Alias, Miriam; Lopez, Maria Pilar; Cativiela, Carlos Tetrahedron, 2004 , vol. 60, # 4 p. 885 - 891

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Citation Number: 9

Abstract

threo and erythro diastereoisomers of the constrained amino acid (βMe) Phe can be obtained separately on a multigram scale through a three-step synthesis from the corresponding Z and E isomers of 2-phenyl-4 (α-phenylethylidene)-5 (4H)-oxazolone. The 5 (4H)-oxazolones are readily available from acetophenone and hippuric acid. The four enantiomerically pure isomers of β-methylphenylalanine,(2R, 3R)-(βMe) Phe,(2S, 3S)-( ...

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