A facile, one-pot synthesis of beta-substituted (Z)-acrylonitriles utilizing an alpha-diaminoboryl carbanion.
A simple three-step single-pot procedure for Z-stereoselective synthesis of beta-monosubstituted acrylonitriles has been established. The reaction involves olefination of aldehydes with an in situ generated alpha-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%).
Tomioka
Takashi
T
Department of Chemistry and Biochemistry, University of Mississippi, University, Mississippi 38677, USA. tomioka@olemiss.edu
Takahashi
Yusuke
Y
Vaughan
Trey G
TG
Yanase
Takayoshi
T
D000097:Acetonitriles / Q000737:chemistry; D000181:Acrylonitrile / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000097:Acetonitriles; D000447:Aldehydes; D000181:Acrylonitrile