Carbon-carbon bond formation in regio- and ...



Title Carbon-carbon bond formation in regio- and stereoselective palladium-catalyzed cyclization of allene-substituted conjugated dienes
Author(s) Jeanne Lofstedt, J. Franzen, J. E. Backvall
Journal The Journal of Organic Chemistry
Date 2001
Volume 66
Issue 24
Start page 8015
End page 8025
Abstract Regio- and stereoselective palladium-catalyzed reactions of allene-substituted 1,3-dienes 1 in acetic acid at room temperature lead to cyclization with formation of a carbon-carbon bond between the middle carbon of the allene and the terminal carbon of the 1,3-diene. Two different types of reactions, both that constitute 1,4-carboacetoxylations of the 1,3-diene, have been developed. In one of the reactions, Pd(II) catalyzes the oxidation of 1 to bicyclic compounds 2, and in the other, Pd(0) catalyzes the transformation of 1 to bicyclic compounds 3. The products 2 are useful for further synthetic transformations and undergo Diels-Alder reactions with dienophiles to give polycyclic ring systems.

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