Citation
Se. Denmark et al., The chemistry of chlorosilyl enolates. 9. Preparation of chlorosilyl enolates, J ORG CHEM, 63(25), 1998, pp. 9517-9523
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263
→ ACNP
Volume
63
Issue
25
Year of publication
1998
Pages
9517 - 9523
Database
ISI
SICI code
0022-3263(199812)63:25<9517:TCOCE9>2.0.ZU;2-5
Abstract
A variety of chlorosilyl enolates has been prepared starting from esters, t
hiol esters, acylsilanes, and ketones. Two general methods are involved, di
rect enolsilylation with trichlorosilyl triflate and diisopropylethylamine,
and a number of methods based on electrophilic substitution of either C- o
r O-silyl or stannyl carbonyl compounds. The most useful method is a Hg(OAc
)(2)-catalyzed trans-silylation from trimethylsilyl to trichlorosilyl enol
ethers, providing a wide range of ketone enolates in good to high yield.