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Palladium-catalyzed, stereoselective rearrangement of a tetracyclic allyl cyclopropane under arylation
Authors:Storsberg Jörg  Yao Min-Liang  Ocal Nüket  de Meijere Armin  Adam Arnold E W  Kaufmann Dieter E
Institution:Institut für Organische Chemie der Technischen Universit?t Clausthal, Leibnizstr. 6, D-38678, Clausthal-Zellerfeld, Germany.
Abstract:The first example of a pi,sigma domino-Heck reaction under concomitant rearrangement of the tetracyclic allylcyclopropane endo,exo-bishomobarrelene (5) is reported; the stereoselective reaction proceeds via an intramolecular insertion of a primarily-formed carbopalladation intermediate into a strained cyclopropane C-C sigma-bond, giving 9.
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