PALLADIUM-CATALYZED CYCLIZATION OF SILYL-SUBSTITUTED BIS(HOMO)PROPARGYLIC ALCOHOLS TO 2,3-DIHYDROFURANS

Authors
SCHABBERT S SCHAUMANN E
Citation
S. Schabbert et E. Schaumann, PALLADIUM-CATALYZED CYCLIZATION OF SILYL-SUBSTITUTED BIS(HOMO)PROPARGYLIC ALCOHOLS TO 2,3-DIHYDROFURANS, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (9), 1998, pp. 1873-1878
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
9
Year of publication
1998
Pages
1873 - 1878
Database
ISI
SICI code
1434-193X(1998):9<1873:PCOSB>2.0.ZU;2-K
Abstract
Ring-opening of oxiranes 1 by the silicon- and sulfur-functionalized p ropargyl anions 2 yields the corresponding alk-4-yn-1-ols 3. Cyclizati on of 3 to 2,3-dihydro-4-phenylthiofurans 5 is achieved by reaction wi th palladium(II) acetate. The corresponding furans 7 are obtained when copper(II) chloride is added to the reaction mixtures.