Synthesis 2005(19): 3327-3334  
DOI: 10.1055/s-2005-870005
PAPER
© Georg Thieme Verlag Stuttgart · New York

Vinylsulfones as Nucleophiles and Michael Acceptors in the Same Step: Stereoselective Synthesis of Amino Acid Precursors

David Díez*a, Pilar Garcíaa, R. F. Moroa, Isidro S. Marcosa, Pilar Basabea, Narciso M. Garridoa, Howard B. Broughtonb, Julio G. Uronesa
a Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, 37008 Salamanca, Spain
Fax: +34(923)294574; e-Mail: ddm@usal.es;
b Lilly, S.A., Avda de la Industria 30, 28108 Alcobendas, Madrid, Spain
Further Information

Publication History

Received 10 February 2005
Publication Date:
24 June 2005 (online)

Abstract

Several precursors of unnatural amino acids have been synthesized by addition of vinyl sulfones to an imine derived from (R)-glyceraldehyde. In these reactions the addition not only takes place in a stereoselective way, but a hydride transfer is also produced giving rise to the saturated sulfones and a new imine.

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Stewart, J. J. J. QCPE program 455.