L??Phenylalanine Cyclohexylamide: A simple and convenient auxiliary for the synthesis of optically pure α, α??disubstituted (R)??and (S)??amino acids

…, C Lehmann, R Ruffieux, P Schönholzer…

Index: Obrecht; Bohdal; Broger; Bur; Lehmann; Ruffieux; Schonholzer; Spiegler; Muller Helvetica Chimica Acta, 1995 , vol. 78, # 3 p. 563 - 580

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Citation Number: 64

Abstract

Abstract This work describes L-phenylalanine cyclohexylamide (5c) as a simple, cheap, and powerful chiral auxiliary for the synthesis of a series of optically pure α, α-disubstituted (R)- and (S)-amino acids of type 1, such as (R)-and (S)-2-methyl-phenylalanine (1a),(R)-and (S)- 2-methyl-2-phenylglycine (1b), and (R)-and (S)-2-methylvaline (1c; Scheme 3). These amino acids were efficiently transformed into the suitably protected and activated amino acid ...