A practical protocol for the highly E-selective formation of aryl-substituted silylketene acetals

Reference:

Harker, W. R. R., Carswell, E. L. and Carbery, D. R., 2010. A practical protocol for the highly E-selective formation of aryl-substituted silylketene acetals. Organic Letters, 12 (16), pp. 3712-3715.

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Official URL:

http://dx.doi.org/10.1021/ol101580y

Abstract

The E/Z-selectivity in the formation of silylketene acetals derived from phenylacetate esters, mediated by LiHMDS, has been studied by in situ NMR techniques. The formation is seen to be highly E-selective with use of the newly developed protocol. Isolated aryl-substituted silylketene acetals are now attainable with high levels of E-geometrical purity in excellent yield.

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