ELECTROPHILIC 5-ENDO-TRIG CYCLIZATIONS OF 2-SILYL-3-ALKENOLS - A STEREOSELECTIVE ROUTE TO POLYSUBSTITUTED TETRAHYDROFURANS

Authors
ANDREY O DUCRY L LANDAIS Y PLANCHENAULT D WEBER V
Citation
O. Andrey et al., ELECTROPHILIC 5-ENDO-TRIG CYCLIZATIONS OF 2-SILYL-3-ALKENOLS - A STEREOSELECTIVE ROUTE TO POLYSUBSTITUTED TETRAHYDROFURANS, Tetrahedron, 53(12), 1997, pp. 4339-4352
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
12
Year of publication
1997
Pages
4339 - 4352
Database
ISI
SICI code
0040-4020(1997)53:12<4339:E5CO2->2.0.ZU;2-Z
Abstract
Electrophilic 5-endo-trig cyclisations of allylsilanes have been carri ed out leading to tri- and tetrasubstituted tetrahydrofurans with reas onable fields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A sili con group having a thienyl fragment attached to the silicon has also b een devised was shown to be oxidized under both electrophilic and nucl eophilic conditions. (C) 1997 Elsevier Science Ltd.