Tertiary Aromatic Amide for Memory of Chirality: Access to Enantioenriched α-Substituted Valine

M Branca, D Gori, R Guillot, V Alezra…

Index: Branca, Mathieu; Gori, Didier; Guillot, Regis; Alezra, Valerie; Kouklovsky, Cyrille Journal of the American Chemical Society, 2008 , vol. 130, # 18 p. 5864 - 5865

Full Text: HTML

Citation Number: 27

Abstract

A new methodology for the asymmetric synthesis of quaternary α-substituted amino acids using memory of chirality has been developed. This strategy employs dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an α-amino acid during the enolization step. Starting from l-valine, an oxazolidin-5-one containing a tertiary aromatic amide was synthesized in one step and then alkylated with various electrophiles with ...