An asymmetric method for the α-oxyacylation of carbonyl compounds.

Knowles, Deborah A. and Matthews, Christopher J. and Tomkinson, Nicholas C. O. (2008) An asymmetric method for the α-oxyacylation of carbonyl compounds. In: American Chemical Society , USA, 2011-03-31.

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Abstract

The development of metal-free processes in org. chem. has received much interest in recent years, following a drive to establish novel, selective transformations that are both cleaner and more efficient. We have recently reported a novel process for the α-oxygenation of carbonyl compds.; important synthetic building blocks more commonly accessed via air-sensitive metal intermediates. This process uses N-methyl-O-benzoyl hydroxylamine hydrochloride 1, the reaction proceeding via a [3,3]-sigmatropic rearrangement of an enamine intermadiate 2 (Figure 1). Reactions proceed in one practical step in the presence of moisture and air, giving the products in good to excellent yield. This talk will describe the development and optimization of an asym. variant of this important reaction through introduction of chirality at the nitrogen substituent of the reagent 3. [on SciFinder(R)]