Abstract
An efficient, general procedure for reductive monoalkyl- ation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O- trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithi- um perchlorate/diethyl ether and trimethylsilyl chloride, followed by BH3·NEt3 reduction, and straightforward workup afforded sec- ondary amines, tertiary amines, N-substituted hydroxylamines, and hydrazines, respectively. Reductive alkylation of a-amino esters with aldehydes afforded the corresponding N-monoalkylated a- amino esters selectively.
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