Issue 23, 1999

Stereoselective intramolecular acylation of γ′-benzoyloxyphosphine oxides with an internal chlorotrimethylsilane trap: isolation of silylated tetrahedral intermediates

Abstract

The kinetic products of the intramolecular acylation of γ′-benzoyloxyphosphine oxides were revealed by conducting the reaction in the presence of an internal trapping agent. A high level of stereocontrol over the formation of both the stereogenic centre α to phosphorus and the hemiacetal centre was observed. The stereochemistry of the products was determined by X-ray crystallography and 1H NMR and the stereoselectivity of the reaction is explained in terms of the known structure and configurational instability of lithiated phosphine oxides.

Supplementary files

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 3413-3424

Stereoselective intramolecular acylation of γ′-benzoyloxyphosphine oxides with an internal chlorotrimethylsilane trap: isolation of silylated tetrahedral intermediates

N. Feeder, G. Hutton, A. Nelson and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, 3413 DOI: 10.1039/A907320E

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