title: An α-diaminoboryl carbanion assisted stereoselective single-pot preparation of α,β-disubstituted acrylonitriles.
abstract: An α-diaminoboryl carbanion-mediated one-pot olefination directly converts an acetonitrile or the homologous nitrile into a series of α,β-disubstituted acrylonitriles in a stereoselective manner. The protocol involves the formation of an α-substituted α-diaminoboryl acetonitrile and subsequent olefination with an aldehyde. The use of an aryl or conjugated aldehyde preferentially leads to a (Z)-acrylonitrile, while an aliphatic aldehyde gave an (E)-isomer as a major product. Two complementary approaches, a linear method and a divergent method, are developed.
authors.affiliation: Department of Chemistry and Biochemistry, University of Mississippi, University, Mississippi 38677, United States. tomioka@olemiss.edu
authors.forename: Takashi
authors.initials: T
authors.lastname: Tomioka
authors.forename: Rambabu
authors.initials: R
authors.lastname: Sankranti
authors.forename: Trey G
authors.initials: TG
authors.lastname: Vaughan
authors.forename: Toshihide
authors.initials: T
authors.lastname: Maejima
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Yanase