ALPHA-TOLYLSULFINYLATION OF KETONES VIA THEIR TRIMETHYLSILYL ENOL ETHERS - ONE-STEP SYNTHESIS OF BETA-KETOSULFOXIDES

Authors
CAPUTO R FERRERI C LONGOBARDO L PALUMBO G PEDATELLA S
Citation
R. Caputo et al., ALPHA-TOLYLSULFINYLATION OF KETONES VIA THEIR TRIMETHYLSILYL ENOL ETHERS - ONE-STEP SYNTHESIS OF BETA-KETOSULFOXIDES, Synthetic communications, 23(11), 1993, pp. 1515-1522
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
23
Issue
11
Year of publication
1993
Pages
1515 - 1522
Database
ISI
SICI code
0039-7911(1993)23:11<1515:AOKVTT>2.0.ZU;2-K
Abstract
Ketones are reported to be conveniently converted into their alpha-tol ylsulfinylated derivatives. This new procedure is based on the reactio n of their corresponding trimethylsilyl enol ethers with p-toluenesulf inyl p-tolylsulfone in the presence of tris(dimethylamino)sulfur trime thylsilyldifluoride (TAS-F). Considering that beta-ketosulfoxides are key intermediates for the preparation of alpha,beta-unsaturated ketone s, this procedure turns out to be of rather broad synthetic relevance.