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

Helen Rachel Lagiakos; Marie-Isabel Aguilar; Patrick Perlmutter

doi:10.1021/jo901717a

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

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

Authors

Helen Rachel Lagiakos¹, Marie-Isabel Aguilar, Patrick Perlmutter

Affiliation

¹ Monash University, Clayton, Victoria, 3800, Australia.

PMID: 19754109
DOI: 10.1021/jo901717a

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Hydroxylamines / chemistry*
Molecular Structure
Stereoisomerism

Substances

Hydroxylamines