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. 2009 Oct 16;74(20):8001-3.
doi: 10.1021/jo901717a.

A mild method for the efficient [3,3]-sigmatropic rearrangement of N,O-diacylhydroxylamines

Helen Rachel Lagiakos  1 , Marie-Isabel Aguilar, Patrick Perlmutter
Affiliations

A mild method for the efficient [3,3]-sigmatropic rearrangement of N,O-diacylhydroxylamines

Helen Rachel Lagiakos et al. J Org Chem. .

Abstract

A mild, general method for the [3,3]-sigmatropic rearrangement of N,O-diacylhydroxylamines, employing a combination of mild base and Lewis acid, is described. Employing stoichiometric amounts of reagents with respect to substrate provides alpha-acyloxyamides, whereas an excess of reagents favors formation of cyclic orthoamides.

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