1-Benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate (BAAOTB) as a selective reducing agent

Abstract

1-Benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate (BAAOTB) 1 generated as white solid from commercially available DABCO and sodium borohydride is found to be a selective and versatile reducing agent. The reagent in t-butanol is very useful for reduction of imines, enamines, oximes, reductive amination of aldehydes and ketones and reductive methylation of amines.