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Synfacts 2010(8): 0931-0931
DOI: 10.1055/s-0030-1257761
DOI: 10.1055/s-0030-1257761
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
A One-Pot Synthesis of (Z)-Acrylonitriles via an α-Diaminoboryl Carbanion
T. Tomioka*, Y. Takahashi, T. G. Vaughan, T. Yanase
The University of Mississippi, USA
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Significance
A three-step, one-pot procedure for the Z-stereoselective synthesis of β-monosubstituted acrylonitriles has been carried out. The reaction involves the olefination of aldehydes with an in situ generated α-diaminoboryl carbanionic species. Various aromatic and aliphatic aldehydes were converted into the corresponding Z-olefin products in good yields.