EU(FOD)(3) AND SNCL4-CATALYZED HETEROCYCLOADDITIONS OF O-SILYL ENOL ETHERS DERIVING FROM CYCLIC-KETONES

Authors
DUJARDIN G MARTEL A BROWN E
Citation
G. Dujardin et al., EU(FOD)(3) AND SNCL4-CATALYZED HETEROCYCLOADDITIONS OF O-SILYL ENOL ETHERS DERIVING FROM CYCLIC-KETONES, Tetrahedron letters, 39(47), 1998, pp. 8647-8650
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
47
Year of publication
1998
Pages
8647 - 8650
Database
ISI
SICI code
0040-4039(1998)39:47<8647:EASHOO>2.0.ZU;2-R
Abstract
O-t-Butyldimethylsilyl enol ethers deriving from simple cyclic ketones acted as efficient dienophiles in the Lewis acid-catalyzed heterocycl oadditions with methyl benzylidenepyruvate 1. Good selectivities were observed with cyclohexanone derivatives. Using Eu(fod)(3), the dienoph ile 2b led to the expected endo adduct 3b (93-97%). When using SnCl4, the major product (89-95%) was found to be the ''abnormal'' adduct 5b with a trans ring junction. (C) 1998 Published by Elsevier Science Ltd . All rights reserved.