Phosphine-Catalyzed Vicinal Acylcyanation of Alkynoates

Phosphine organocatalysis enabled vicinal acylcyanation of alkynoates with acyl cyanides to form acrylonitrile derivatives with a tetrasubstituted alkene moiety. The acyl and cyano groups were introduced at the α and β carbon atoms, respectively, of the C–C triple bond in the alkynoates with complet...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (7), p.1706-1709
Main Authors: Murayama, Hiroaki, Nagao, Kazunori, Ohmiya, Hirohisa, Sawamura, Masaya
Format: Article
Language:English
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Summary:Phosphine organocatalysis enabled vicinal acylcyanation of alkynoates with acyl cyanides to form acrylonitrile derivatives with a tetrasubstituted alkene moiety. The acyl and cyano groups were introduced at the α and β carbon atoms, respectively, of the C–C triple bond in the alkynoates with complete regioselectivity and high anti stereoselectivity. A variety of functional groups in the acyl cyanides and alkynoates were tolerated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00677