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A Facile, One-Pot Synthesis of β-Substituted (Z)-Acrylonitriles Utilizing an α-Diaminoboryl Carbanion

Takashi Tomioka*, Yusuke Takahashi, Trey G. Vaughan and Takayoshi Yanase

*Department of Chemistry and Biochemistry, University of Mississippi, University, Mississippi 38677, Email: tomiokaolemiss.edu

T. Tomioka, Y. Takahashi, T. G. Vaughan, T. Yanase, Org. Lett., 2010, 12, 2171-2173.

DOI: 10.1021/ol100534s


Abstract

A simple three-step single-pot procedure for Z-stereoselective synthesis of β-monosubstituted acrylonitriles involves olefination of aldehydes with an in situ generated α-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly converted into the corresponding (Z)-olefin products in good yields.

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Key Words

vinyl nitriles


ID: J54-Y2010-1320