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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title = "A practical protocol for the highly E-selective formation of aryl-substituted silylketene acetals",

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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T1 - A practical protocol for the highly E-selective formation of aryl-substituted silylketene acetals

AU - Harker, Wesley R R

AU - Carswell, E L

AU - Carbery, David R

PY - 2010/8/20

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.

UR - https://www.scopus.com/pages/publications/77955679843

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

U2 - 10.1021/ol101580y

DO - 10.1021/ol101580y

M3 - Article

SN - 1523-7060

VL - 12

SP - 3712

EP - 3715

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

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

Abstract

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