A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids

AM Nocioni, C Papa, C Tomasini

Index: Nocioni, Alessandra Maria; Papa, Carmela; Tomasini, Claudia Tetrahedron Letters, 1999 , vol. 40, # 48 p. 8453 - 8456

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Citation Number: 24

Abstract

The diastereoselective synthesis of syn-α-alkyl α-hydroxy β-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti α-alkyl β- benzoylamino acid methyl esters with iodine. The intermediate α-iodo derivatives spontaneously afforded cis-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99: 1.