Synthesis 2006(24): 4151-4158  
DOI: 10.1055/s-2006-950367
PAPER
© Georg Thieme Verlag Stuttgart · New York

Precursors of Chiral α-Amino Anions: An Improved Synthesis of Chiral N-(α-Tributylstannylorgano)oxazolidin-2-ones Derived from (R)- or (S)-Phenylglycinol

Vincent Coeffard, Erwan Le Grognec*, Isabelle Beaudet, Marc Lepeltier, Véronique Léat-Crest, Jean-Paul Quintard*
Université de Nantes, Nantes Atlantique Universités, CNRS, Faculté des Sciences et des Techniques, Laboratoire de Synthèse Organique (LSO), UMR CNRS 6513, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
Fax: +33(2)51125402; e-Mail: erwan.legrognec@univ-nantes.fr; e-Mail: jean-paul.quintard@univ-nantes.fr;
Further Information

Publication History

Received 12 July 2006
Publication Date:
13 November 2006 (online)

Abstract

A convenient and versatile method for the synthesis of N-(α-tributylstannylorgano)oxazolidin-2-ones under mild experimental conditions is described. Treatment of various N-(α-tributylstannylorgano)phenylglycinol carbamates with sodium hydride in DMF or with mesyl chloride/triethylamine in dichloromethane at room temperature affords the functionalized N-(α-tributylstannylorgano)oxazolidin-2-ones in yields up to 90%. Their subsequent transmetalation reaction, leading to chiral α-amino anions, is briefly discussed.