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

Wesley R R Harker; E L Carswell; David R Carbery

doi:10.1021/ol101580y

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

Wesley R R Harker, E L Carswell, David R Carbery

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

17 Citations (SciVal)

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.

Original language	English
Pages (from-to)	3712-3715
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	16
DOIs	https://doi.org/10.1021/ol101580y
Publication status	Published - 20 Aug 2010

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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.",

author = "Harker, {Wesley R R} and Carswell, {E L} and Carbery, {David R}",

year = "2010",

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AU - Harker, Wesley R R

AU - Carswell, E L

AU - Carbery, David R

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Y1 - 2010/8/20

N2 - 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.

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

Abstract

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