Organic letters

Mild nonepimerizing N-alkylation of amines by alcohols without transition metals

C Guérin, V Bellosta, G Guillamot, J Cossy

Index: Guerin, Claire; Bellosta, Veronique; Guillamot, Gerard; Cossy, Janine Organic Letters, 2011 , vol. 13, # 13 p. 3534 - 3537

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Citation Number: 21

Abstract

Here, we report a one-pot oxidation/imine-iminium formation/reduction sequence under mild conditions (Scheme 1). This sequence allows the chemoselective N-alkylation of amines with various nonactivated primary and secondary alcohols and prevents epimerization of optically active substrates (amines or alcohols). Furthermore, no transition metals are involved which is of importance when medicinal chemists have to prepare amines for biological tests.