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Synthesis 2009(14): 2365-2370  
DOI: 10.1055/s-0029-1216827
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphine-Catalyzed Reaction of Cyanohydrins with Activated Alkynes

Acétou Siby, Olivier Loreau*, Frédéric Taran*
CEA, IBITECS, Service de Chimie Bioorganique et de Marquage, Gif sur Yvette, 91191, France
Fax: +33(1)69087991; e-Mail: frederic.taran@cea.fr;
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Publikationsverlauf

Received 29 March 2009
Publikationsdatum:
25. Mai 2009 (online)

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Abstract

A new method for preparing α-cyanoacrylates and α-cyanoenones is described. The procedure uses a phosphine-catalyzed α-C addition of cyanide ion, generated in situ from cyanohydrins, to activated alkynes. An unexpected tandem reaction producing benzylidenecyclopentanones is also described.

Key words

cyanoacrylates - alkynes - catalysis - phosphines

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