Reaction of oximes and α-hydroxyimino ketones with aqueous alkaline sodium borohydride

Abstract

Reaction of saturated oximes with aqueous alkaline sodium borohydride at reflux gives the corresponding alcohols in good yields whereas oximes of conjugated carbonyl compounds do not react. α-Hydroxyimino ketones (1) yield 1,2-diols in good yields under the above conditions.

The synthetic applications and a possible mechanism of these reductions are discussed.