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

David Díez; Pilar García; R. F. Moro; Isidro S. Marcos; Pilar Basabe; Narciso M. Garrido; Howard B. Broughton; Julio G. Urones

doi:10.1055/s-2005-870005

PAPER

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

David Díez*^a, Pilar García^a, R. F. Moro^a, Isidro S. Marcos^a, Pilar Basabe^a, Narciso M. Garrido^a, Howard B. Broughton^b, Julio G. Urones^a
^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

Abstract

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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.

Key words

vinyl sulfones - hydride transfer - stereoselectivity - synthesis - amino acids - molecular model - transition state

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References

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