PALLADIUM-CATALYZED STEREOCONTROLLED ENDO CYCLIZATION OF 3-HYDROXYPROPYL-1,3-CYCLOHEXADIENE LEADING TO VERSATILE FUSED TETRAHYDROPYRANS

Authors
KOROLEVA EB BACKVALL JE ANDERSSON PG
Citation
Eb. Koroleva et al., PALLADIUM-CATALYZED STEREOCONTROLLED ENDO CYCLIZATION OF 3-HYDROXYPROPYL-1,3-CYCLOHEXADIENE LEADING TO VERSATILE FUSED TETRAHYDROPYRANS, Tetrahedron letters, 36(30), 1995, pp. 5397-5400
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
30
Year of publication
1995
Pages
5397 - 5400
Database
ISI
SICI code
0040-4039(1995)36:30<5397:PSECO3>2.0.ZU;2-B
Abstract
A palladium-catalyzed synthesis of stereodefined fused tetrahydropyran s from 2-substituted 1,3-cyclohexadienes is presented. The reaction ta kes place via an intramolecular 1,4-oxidation of the conjugated diene via a (pi-allyl)palladium intermediate. The stereochemical outcome of the reaction can be controlled to give either cis or trans 1,4-additio n over the conjugated diene. The structure of the products was establi shed by X-ray crystallography.