Memory of chirality of tertiary aromatic amides: a simple and efficient method for the enantioselective synthesis of quaternary α-amino acids

…, R Guillot, D Gori, V Alezra, C Kouklovsky

Index: Branca, Mathieu; Pena, Sebastien; Guillot, Regis; Gori, Didier; Alezra, Valerie; Kouklovsky, Cyrille Journal of the American Chemical Society, 2009 , vol. 131, # 30 p. 10711 - 10718

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Citation Number: 40

Abstract

A new methodology for the asymmetric synthesis of quaternary α-substituted amino acids using memory of chirality has been developed. The strategy utilizes the dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an α-amino acid during an enolization step. Starting from five different l-amino acids, the corresponding oxazolidin-5- ones containing a tertiary aromatic amide group have been synthesized in one step and ...