PAPER	Synthesis 2003: 2206-2210   DOI: 10.1055/s-2003-41066
© Georg Thieme Verlag Stuttgart · New York
Selective Access to Secondary Amines by a Highly Controlled Reductive Mono-N-Alkylation of Primary Amines
Hephzibah J. Kumpatya, Sukanta Bhattacharyya*b, Erik W. Rehra, Amelia M. Gonzaleza
a Department of Chemistry, University of Wisconsin-Whitewater, WI-53190, USA b Argonaut Technologies, 1101 Chess Drive, Foster City, CA 94404, USA e-Mail: sbhattacharyya@argotech.com;
Received 20 May 2003

Abstract

A selective and direct access to secondary amines is reported by reductive mono-N-alkylation of primary amines in the presence of Ti(i-PrO)₄ and NaBH₄. Secondary amines are obtained exclusively from a set of carbonyl compounds and primary amines, demonstrating high chemoselectivity toward reductive mono-N-alkylation.

Key Words

mono-N-alkylation - secondary amines - titanium(IV) isopropoxide - sodium borohydride