A catalytic asymmetric synthesis of N-Boc-β-Methylphenylalanines

…, A Moyano, MA Pericàs, A Riera

Index: Pasto, Mireia; Moyano, Albert; Pericas, Miquel A.; Riera, Antoni Journal of Organic Chemistry, 1997 ,  vol. 62,  # 24  p. 8425 - 8431

Full Text: HTML

Citation Number: 27

Abstract

An efficient, stereodivergent, and enantioselective synthesis of the syn and anti diastereomers of N-Boc-β-methylphenylalanine has been developed. Starting from enantiomerically pure (2 S, 3 S)-2, 3-epoxy-3-phenyl-1-propanol, a three-step sequence, consisting of the oxidation of the primary alcohol up to the carboxyl stage, ring opening of the epoxy acid with Me2CuCNLi2, and esterification of the resulting hydroxy acid with ...