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Synlett 2011(16): 2321-2324  
DOI: 10.1055/s-0030-1261217
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Thermal [2+2] Cycloaddition of CF3-Substituted Allenynes: Access to Novel Cyclobutene-Containing α-Amino Acids

Artur K. Mailyana, Ivan M. Krylova, Christian Bruneaub, Pierre H. Dixneufb, Sergey N. Osipov*a
a A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russian Federation
Fax: +7(499)1355085; e-Mail: osipov@ineos.ac.ru;
b Institute Sciences Chimiques de Rennes, UMR 6226 CNRS-Universite de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France
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Publication History

Received 27 June 2011
Publication Date:
08 September 2011 (online)

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Abstract

An efficient approach for the preparation of novel CF3-substituted cyclic α-amino acid derivatives fused with cyclobutene ring has been developed. The method is based on intramolecular thermal [2+2] cycloaddition of amino acid containing allenynes with internal triple bond obtained by successive [2,3]-sigmatropic rearrangement of propargyl-containing nitrogen CF3-ylides and ­Sonogashira derivatization of the triple bond.

Key words

allenynes - Sonogashira coupling - [2+2] cycloaddition - cyclobutenes - amino acids

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