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

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

A simple three-step single-pot procedure for Z-stereoselective synthesis of β-monosubstituted acrylonitriles has been established. The reaction involves olefination of aldehydes with an in situ generated α-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly convert...

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Veröffentlicht in:Organic letters 2010-05, Vol.12 (10), p.2171-2173
Hauptverfasser: Tomioka, Takashi, Takahashi, Yusuke, Vaughan, Trey G, Yanase, Takayoshi
Format: Artikel
Sprache:eng
Schlagworte:
Acetonitriles - chemistry
Acrylonitrile - analogs & derivatives
Acrylonitrile - chemical synthesis
Acrylonitrile - chemistry
Aldehydes - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:A simple three-step single-pot procedure for Z-stereoselective synthesis of β-monosubstituted acrylonitriles has been established. The reaction 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 (up to 96:4 ratio) in good yields (80−98%).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100534s