Regioselective alpha-alkylation of silyl enolates using a mild catalyst- ZnCl2 doped on acidic alumina

Authors
Kad, GL Singh, V Khurana, A Chaudhary, S Singh, J
Citation
Gl. Kad et al., Regioselective alpha-alkylation of silyl enolates using a mild catalyst- ZnCl2 doped on acidic alumina, SYN COMMUN, 29(19), 1999, pp. 3439-3442
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
19
Year of publication
1999
Pages
3439 - 3442
Database
ISI
SICI code
0039-7911(1999)29:19<3439:RAOSEU>2.0.ZU;2-#
Abstract
ZnCl2 doped acidic alumina used as a solid support acts as a better Lewis a cid in the S(N)1 reaction of trimethyl silyl enol ethers with 3(0),allylic and benzylic halides to yield exclusively the substituted product in excell ent yields, This method has been employed for the synthesis of monocyclic s esquitepene hydrocarbon, (+/-)-beta-bisabolene and a monoterpene, 2,6-dimet hyl-7-octen-4-one.