Issue 31, 2005
From the journal:

Chemical Communications

New synthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one under stereospecific constraints induced by host–guest interactions†

Arnaud Grandeury,a   Samuel Petit,b   Servane Coste,b   Gérard Coquerel,b   Cécile Perrioc  and  Géraldine Gouhier*d  

* Corresponding authors

a Max-Planck-Institut für Dynamic komplexer technischer Systeme, Sandorstraße 1, Magdeburg, Germany

b UPRES EA 3233, SMS, IRCOF, Université de Rouen, 1 Rue Tesnière, Mont Saint Aignan cedex, France

c UMR CEA, Centre Cycéron, Bd H. Becquerel, BP 5229, Caen Cedex, France

d UMR CNRS 6014, LFAOC, IRCOF, Université de Rouen, 1 Rue Tesnière, Mont Saint Aignan cedex, France
E-mail: geraldine.gouhier@univ-rouen.fr
Fax: (+33) 2 35 52 29 71
Tel: (+33) 2 35 52 24 67

Abstract

A selective, efficient, and fast access to (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one (BCBCH), precursor of the synthetic antagonist of tissue-plasminogen activator (t-PA), is reported using a solid/solid aldolisation–crotonisation reaction on a supramolecular complex under microwave irradiation. The underlying mechanism is investigated from the crystal structure of the intermediate host–guest complex formed between permethylated γ-cyclodextrin and (Z)-2-(4-cyanobenzylidene)cycloheptan-1-one.

Graphical abstract: New synthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one under stereospecific constraints induced by host–guest interactions

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Article information

DOI
https://doi.org/10.1039/B504989J
Article type
Communication
Submitted
12 Apr 2005
Accepted
13 Jun 2005
First published
12 Jul 2005

Chem. Commun., 2005, 4007-4009

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New synthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one under stereospecific constraints induced by host–guest interactions

A. Grandeury, S. Petit, S. Coste, G. Coquerel, C. Perrio and G. Gouhier, Chem. Commun., 2005, 4007 DOI: 10.1039/B504989J

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