Mild Nonepimerizing N-Alkylation of Amines by Alcohols without Transition Metals

Claire Guérin, Véronique Bellosta, Gérard Guillamot and Janine Cossy*

*Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS UMR 7084, 10 rue Vauquelin, 75231-Paris Cedex 05, France, and PCAS, 23 rue Bossuet, Z.I. la vigne aux Loups, 91160-Longjumeau, France, Email: janine.cossyespci.fr

C. Guérin, V. Bellosta, G. Guillamot, J. Cossy, Org. Lett., 2011, 13, 3478-3481.

DOI: 10.1021/ol201351a

Abstract

A one-pot two-step sequence involving an oxidation/imine-iminium formation/reduction allowed the N-alkylation of amines by alcohols. Optically active alcohols and amines can be converted without any epimerization.

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Key Words

amines, TEMPO, iodosobenzene diacetate, sodium triacetoxyborohydride

ID: J54-Y2011-1960