STEREOSELECTIVE SYNTHESIS OF (Z)-ALPHA-(ALKOXYCARBONYL)METHYLENE BETA-LACTONES AND GAMMA-LACTONES BY PALLADIUM-CATALYZED OXIDATIVE CARBONYLATION OF ALKYNOLS

Authors
GABRIELE B SALERNO G DEPASCALI F COSTA M CHIUSOLI GP
Citation
B. Gabriele et al., STEREOSELECTIVE SYNTHESIS OF (Z)-ALPHA-(ALKOXYCARBONYL)METHYLENE BETA-LACTONES AND GAMMA-LACTONES BY PALLADIUM-CATALYZED OXIDATIVE CARBONYLATION OF ALKYNOLS, Journal of the Chemical Society. Perkin transactions. I, (2), 1997, pp. 147-154
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
2
Year of publication
1997
Pages
147 - 154
Database
ISI
SICI code
0300-922X(1997):2<147:SSO(B>2.0.ZU;2-G
Abstract
(Z)-alpha-(Alkoxycarbonyl)methylene beta- and gamma-lactones can be ob tained in fair to excellent yields and with high catalytic efficiencie s by PdI2/KI-catalysed oxidative dialkoxycarbonylation of propynyl alc ohols (alpha,alpha-dialkyl substituted, or alpha-monoalkyl substituted with a sufficiently bulky alkyl group) and but-3-yn-1-ols, respective ly. Reactions are carried out in alcoholic media under mild conditions (70-80 degrees C and 20 atm of a 3:1 mixture of carbon monoxide and a ir). Reaction pathways are discussed.