Chemoselective Reductive Alkylation of Ammonia with Carbonyl Compounds: Synthesis of Primary and Symmetrical Secondary Amines
An efficient, general procedure for highly chemoselective reductive mono-alkylation of ammonia with ketones is reported. Treatment of ketones with ammonia in ethanol and titanium(IV) isopropoxide, followed by in situ sodium borohydride reduction, and a straightforward workup afforded primary amines in good to excellent yields. Reductive alkylation of ammonia with aldehydes, on the other hand, afforded the corresponding symmetrical secondary amines selectively.
Copyright © 2003, Elsevier
Miriyala, Bruhaspathy; Bhattacharyya, Sukanta; and Williamson, John S., "Chemoselective Reductive Alkylation of Ammonia with Carbonyl Compounds: Synthesis of Primary and Symmetrical Secondary Amines" (2004). Office for Research Publications and Presentations. 23.