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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Authors: | Grandeury Arnaud Petit Samuel Coste Servane Coquerel Gérard Perrio Cécile Gouhier Géraldine |
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Affiliation: | Max-Planck-Institut für Dynamic komplexer technischer Systeme, Sandorstrasse 1, D-39106, Magdeburg, Germany. |
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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. |
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