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

Arnaud Grandeury; Samuel Petit; Servane Coste; Gérard Coquerel; Cécile Perrio; Géraldine Gouhier

doi:10.1039/b504989j

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

Chem Commun (Camb). 2005 Aug 21:(31):4007-9. doi: 10.1039/b504989j. Epub 2005 Jul 12.

Authors

Arnaud Grandeury¹, Samuel Petit, Servane Coste, Gérard Coquerel, Cécile Perrio, Géraldine Gouhier

Affiliation

¹ Max-Planck-Institut für Dynamic komplexer technischer Systeme, Sandorstrasse 1, D-39106, Magdeburg, Germany.

PMID: 16075101
DOI: 10.1039/b504989j

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 gamma-cyclodextrin and (Z)-2-(4-cyanobenzylidene)cycloheptan-1-one.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cycloheptanes / chemical synthesis*
Microwaves
Models, Molecular
Stereoisomerism

Substances

2,7-bis(4-cyanobenzylidene)cycloheptan-1-one
Cycloheptanes