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Palladium-catalyzed, stereoselective rearrangement of a tetracyclic allyl cyclopropane under arylation†
Jörg Storsberg,Min-Liang Yao,Nüket Öcal,Armin de Meijere,Arnold E. W. Adam,Dieter E. Kaufmann
Chemical Communications Pub Date : 10/14/2005 00:00:00 , DOI:10.1039/B507732J
Abstract

The first example of a π,σ 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 σ-bond, giving 9.

Graphical abstract: Palladium-catalyzed, stereoselective rearrangement of a tetracyclic allyl cyclopropane under arylation
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