Synthesis and hydrolytic stability of tert-butoxydimethylsilyl enol ethers

Authors
Fataftah, ZA Rawashdeh, AMM Sotiriou-Leventis, C
Citation
Za. Fataftah et al., Synthesis and hydrolytic stability of tert-butoxydimethylsilyl enol ethers, SYN COMMUN, 31(15), 2001, pp. 2379-2389
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
15
Year of publication
2001
Pages
2379 - 2389
Database
ISI
SICI code
0039-7911(2001)31:15<2379:SAHSOT>2.0.ZU;2-T
Abstract
tert-Butoxydimethylsilyl enol ethers derived from aldehydes and ketones wer e synthesized in good yields with high regio- and stereoselectivities, unde r thermodynamically and kinetically controlled conditions. The hydrolytic s tability of tert-butoxydimethylsilyl enol ether of cyclohexanone was studie d under acidic and basic conditions and compared to that of trimethylsilyl, tert-butyldimethylsilyl and (2,4,6-tri-tert-butylphenoxy)dimethylsilyl eno l ethers.