Direct Hydroxymethylation of C=N Double Bonds

Direct hydroxymethylation of C=N double bonds including imines, nitrones, oximes, hydrazones and iminium salts is a less explored synthetic approach to 1,2-amino alcohols that provides good alternatives to the classical methods. The review deals with nucleophilic additions of organometallic hydroxymethyl reagents and lithiated alkoxyallenes to C=N double bonds. Reductive cross couplings between C=N double bonds and aldehydes or ketones are also discussed.