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Synthesis 2004(15): 2545-2549  
DOI: 10.1055/s-2004-831216
PAPER
© Georg Thieme Verlag Stuttgart · New York

Unexpected Addition of Methyl 3,3,3-Trifluoropyruvate to ‘Push-Pull’ Enamines Having a Methyl Group at α-Position

Dmitriy M. Volochnyuk, Aleksandr N. Kostyuk*, Dmitriy A. Sibgatulin, Aleksandr E. Petrenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02094, Ukraine
Fax: +38(44)5373253; e-Mail: a.kostyuk@enamine.net;
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Publication History

Received 19 April 2004
Publication Date:
16 September 2004 (online)

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Abstract

The reaction of ‘push-pull’ enamines having a methyl group at the α-position with methyl 3,3,3-trifluoropyruvate was investigated. As a result, unexpected addition of pyruvate to methyl group was found and a set of polyfunctionalized β-dicarbonyl compounds was obtained. Possible mechanism of the reaction is discussed.

Key words

‘push-pull’ enamines - methyl 3,3,3-trifluoropyruvate - nucleophilic addition - ene reaction

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