PALLADIUM-CATALYZED ALKYLATION OF CYCLOALKENES

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Progress in medicine today relies heavily on the development in synthetic organic chemistry of new chemo-, stereo- and regioselective methods for the synthesis of carbon-carbon bonds. Preliminary results in our laboratories indicate that the palladium-catalyzed allylic cross-coupling of cyclic alkenes and aryl, vinylic and alkynyl halides, as well as alkenyl triflates, can be effected in high yield, under mild reaction conditions, free of isomers. The ability of organopalladium compounds to accommodate a wide variety of important organic functional groups and their tendency to add to alkenes with high regio- and stereoselectivity suggest this to be an exceptionally useful new approach to carbon-carbon bond formation which cannot be effected in any other way by present methodology. A detailed study of the scope and limitations of this process is proposed. Intramolecular variations of this process will be examined. Hetero- and carboannulation sequences utilizing this chemistry look particularly promising. This new methodology possesses vast potential for the synthesis of such diverse medicinally and physiologically interesting substances as alkaloids, cannabinoids, prostaglandins and polycyclic aromatic hydrocarbons.