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Synthesis 2008(5): 743-746  
DOI: 10.1055/s-2008-1032171
PAPER
© Georg Thieme Verlag Stuttgart · New York

Formal [2+2] Cycloaddition of 2-(Acylamino)acrylates with Vinyl Sulfides: An Approach to Cyclobutane α-Amino Acids as S-Phenylcysteine Analogues

Alberto Avenoza, Jesús H. Busto*, Lara Mata, Jesús M. Peregrina*, Marta Pérez-Fernández
Departamento de Química, UA-CSIC, Universidad de La Rioja, 26006 Logroño, Spain
Fax: +34(941)299621; e-Mail: hector.busto@unirioja.es; e-Mail: jesusmanuel.peregrina@unirioja.es;
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Publication History

Received 11 October 2007
Publication Date:
08 February 2008 (online)

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Abstract

Two new types of conformationally restricted S-phenylcysteine are presented. The restriction comprises a cyclobutane unit that includes the α- and β-carbons of the α-amino acid. The synthetic strategy is based on a formal [2+2] cycloaddition between 2-(acyl­amino)acrylates as acceptor alkenes and vinyl sulfides as donor alkenes, promoted by aluminum-derived bulky Lewis acids.

Key words

cycloadditions - Michael additions - aldol reaction - aluminum - amino acids - cysteine