Issue 9, 2001

Chiral organometallic reagents. Part 27.1 The stereochemistry of the carbomagnesiation of a vinylsilane

Abstract

The intramolecular carbomagnesiation of a vinylsilane at 25 °C in THF has been found to proceed in a stereospecific (>95%) syn-addition of carbon and magnesium to the double bond. The resulting α-silylalkylmagnesium compounds are not configurationally stable under the reaction conditions. They epimerize with a half-life of 2.7 d at room temperature.

Graphical abstract: Chiral organometallic reagents. Part 27.1 The stereochemistry of the carbomagnesiation of a vinylsilane

Article information

Article type
Paper
Submitted
26 Apr 2001
Accepted
13 Jun 2001
First published
24 Jul 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 1785-1792

Chiral organometallic reagents. Part 27. The stereochemistry of the carbomagnesiation of a vinylsilane

R. W. Hoffmann, O. Knopff and T. Faber, J. Chem. Soc., Perkin Trans. 2, 2001, 1785 DOI: 10.1039/B103801J

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