CYCLIZATIONS OF 5-SILYL-SUBSTITUTED 4,5-EPOXY-1-ALKANOLS - A CONFIGURATION DEPENDENT MODE OF RING-CLOSURE

Authors
ADIWIDJAJA G FLORKE H KIRSCHNING A SCHAUMANN E
Citation
G. Adiwidjaja et al., CYCLIZATIONS OF 5-SILYL-SUBSTITUTED 4,5-EPOXY-1-ALKANOLS - A CONFIGURATION DEPENDENT MODE OF RING-CLOSURE, Tetrahedron letters, 36(48), 1995, pp. 8771-8774
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
48
Year of publication
1995
Pages
8771 - 8774
Database
ISI
SICI code
0040-4039(1995)36:48<8771:CO54-A>2.0.ZU;2-A
Abstract
The preparation and proton-induced cyclization of silyl-substituted 4, 5-epoxy-1-alkanols is described The regioselectivity of intramolecular attack of the hydroxy group an the epoxy silane moiety is highly depe ndent on the configuration of the epoxy alcohols employed. Thus 1,4-an ti epoxy alcohols exclusively yield tetrahydropyrans whereas the corre sponding 1,4-syn derivates furnish a diastereomeric mixture of tetrahy drofurans.