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