Novel chiral hydroxylamines for the asymmetric α-functionalisation of carbonyl compounds.

We have recently reported a family of hydroxylamine based reagents for the α-oxyacylation, α-oxycarbonylation, α-oxycarbamoylation and α-oxytosylation of carbonyl compds. These reagents have been shown to react with both aldehydes and ketones to generate α-functionalised products under mild, practical conditions in good to excellent yields (Figure 1). It is believed that each of these transformations proceed via a common [3,3]-sigmatropic rearrangement process, which revealed the opportunity to develop asym. variants of each reaction which would significantly add to the synthetic chemist's tool box. This poster will describe the development of asym. variants of these reactions through introduction of chirality in the generic reagent 1 at the nitrogen substituent (R3), oxygen substituent (R4) and the co-acid (HX). [on SciFinder(R)]