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Synfacts 2007(5): 0494-0494  
DOI: 10.1055/s-2007-968451
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

E-Olefins: Reaction of Nitrones with Free and Pt-Coordinated Nitriles

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
J. Lasri, M. A. J. Charmier*, M. Haukka, A. J. L. Pombeiro*
Instituto Superior Técnico and Universidade Lusófona de Humanidades e Tecnologias, Lisbon, Portugal; Univeristy of Joensuu, Finland
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

Organonitriles with acidic α-methylene protons showed interesting dual reactivity where both the methylene group and cyano group react under platinum catalysis. One important aspect is to use less reactive acyclic nitrones. Microwave irradiation was shown to significantly enhance the rate and yield of the reactions compared­ to normal reflux conditions. When precomplexed Pt-organonitrile substrates were used, the reaction showed a preference for the [3+2] cycloaddition product complexed to Pt(II). After prolonged heating the [3+2] adduct reverts to the thermodynamically favored cyanoalkene.