title: New synthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one under stereospecific constraints induced by host-guest interactions.
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.
authors.affiliation: Max-Planck-Institut für Dynamic komplexer technischer Systeme, Sandorstrasse 1, D-39106, Magdeburg, Germany.
authors.forename: Arnaud
authors.initials: A
authors.lastname: Grandeury
authors.forename: Samuel
authors.initials: S
authors.lastname: Petit
authors.forename: Servane
authors.initials: S
authors.lastname: Coste
authors.forename: Gérard
authors.initials: G
authors.lastname: Coquerel
authors.forename: Cécile
authors.initials: C
authors.lastname: Perrio
authors.forename: Géraldine
authors.initials: G
authors.lastname: Gouhier
mesh_terms: D003508:Cycloheptanes / Q000138:chemical synthesis*; D008872:Microwaves; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: C519114:2,7-bis(4-cyanobenzylidene)cycloheptan-1-one; D003508:Cycloheptanes