Chemistry Letters, Vol.48, No.8, 965-967, 2019
Generation of Boron Aza-Enolates by a Nickel-catalyzed Reaction of Triazoles with Pinacolborane and Their Addition to Aldehydes
An aldol-type reaction of boron aza-enolates with aldehydes is reported. N-Sulfonyl-1,2,3-triazoles react with pinacolborane in the presence of a nickel(0) catalyst to generate boron azaenolates with E geometry. The boron aza-enolates undergo an aldol-type reaction with aldehydes to give beta-boroxy imines with syn configuration. The subsequent one-pot reduction with DIBALH gives 1,3-amino alcohols.