n-BuLi/LiCH2CN-mediated one-carbon homologation of aryl epoxides into conjugated allyl alcohols.

A series of styrene oxides in the presence of a 1:1 mixture of n-butyllithium (n-BuLi) and lithioacetonitrile (LiCH2CN) in THF are converted into one-carbon homologated allyl alcohols in an unusual regioselective manner.

An α-diaminoboryl carbanion assisted stereoselective single-pot preparation of α,ß-disubstituted acrylonitriles.

An α-diaminoboryl carbanion-mediated one-pot olefination directly converts an acetonitrile or the homologous nitrile into a series of α,ß-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.