Chemoselective reductive alkylation of ammonia with carbonyl compounds: synthesis of primary and symmetrical secondary amines

B Miriyala, S Bhattacharyya, JS Williamson

Index: Miriyala, Bruhaspathy; Bhattacharyya, Sukanta; Williamson, John S. Tetrahedron, 2004 , vol. 60, # 7 p. 1463 - 1471

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Citation Number: 149

Abstract

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 ...