SILICON-DIRECTED CYCLIZATION OF VINYLSILANES BEARING HYDROXY GROUP CATALYZED BY AN ACID

Authors
MIURA K OKAJIMA S HONDO T HOSOMI A
Citation
K. Miura et al., SILICON-DIRECTED CYCLIZATION OF VINYLSILANES BEARING HYDROXY GROUP CATALYZED BY AN ACID, Tetrahedron letters, 36(9), 1995, pp. 1483-1486
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
9
Year of publication
1995
Pages
1483 - 1486
Database
ISI
SICI code
0040-4039(1995)36:9<1483:SCOVBH>2.0.ZU;2-I
Abstract
Silicon-directed stereoselective syn addition of hydroxy group to olef inic double bond occurs intramolecularly in an acid-catalyzed cyclizat ion of vinylsilanes bearing hydroxy group. Thus 5-dimethylphenylsilyl- 4-penten-1-ol is smoothly cyclized to 2-(dimethylphenylsilyl)methyltet rahydrofuran upon the treatment of a catalytic amount of p-toluenesulf onic acid (TsOH) or TiCl4.