Issue 45, 2005
From the journal:

Chemical Communications

Palladium-catalyzed, stereoselective rearrangement of a tetracyclic allyl cyclopropane under arylation†

Jörg Storsberg,a   Min-Liang Yao,a   Nüket Öcal,a   Armin de Meijere,b   Arnold E. W. Adamc  and  Dieter E. Kaufmann*a  

* Corresponding authors

a Institut für Organische Chemie der Technischen Universität Clausthal, Leibnizstr. 6, Clausthal-Zellerfeld, Germany
E-mail: dieter.kaufmann@tu-clausthal.de
Fax: +49 5323 722834
Tel: +49 5323 722027

b Institut für Organische Chemie der Universität Göttingen, Tammannstr. 2, Göttingen, Germany
E-mail: armin.demeijere@chemie.uni-goettingen.de
Fax: +49 551 399475
Tel: +49 551 393231

c Institut für Anorganische und Analytische Chemie der Technischen Universität Clausthal, Paul-Ernst-Str. 4, Clausthal-Zellerfeld, Germany
E-mail: arnold.adam@tu-clausthal.de
Fax: +49 5323 722995
Tel: +49 5323 722227

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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Article information

DOI
https://doi.org/10.1039/B507732J
Article type
Communication
Submitted
02 Jun 2005
Accepted
20 Sep 2005
First published
14 Oct 2005

Chem. Commun., 2005, 5665-5666

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

J. Storsberg, M. Yao, N. Öcal, A. de Meijere, A. E. W. Adam and D. E. Kaufmann, Chem. Commun., 2005, 5665 DOI: 10.1039/B507732J

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