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

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.