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

Authors
Hoffmann, RW Knopff, O Faber, T
Citation
Rw. Hoffmann et al., Chiral organometallic reagents. Part 27. The stereochemistry of the carbomagnesiation of a vinylsilane, J CHEM S P2, (9), 2001, pp. 1785-1792
Citations number
72
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
ISSN journal
1472779X → ACNP
Issue
9
Year of publication
2001
Pages
1785 - 1792
Database
ISI
SICI code
1472-779X(200109):9<1785:CORP2T>2.0.ZU;2-L
Abstract
The intramolecular carbomagnesiation of a vinylsilane at 25 degreesC in THF has been found to proceed in a stereospecific(>95%) syn-addition of carbon and magnesium to the double bond. The resulting alpha -silylalkylmagnesium compounds are not configurationally stable under the reaction conditions. They epimerize with a half-life of 2:7 d at room temperature.