A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles

A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reac-tive cycloheptadiene, which concomitantly underg...

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Detalles Bibliográficos
Autores: Artigas Ruf, Albert, Vila Vadrí, Jordi, Lledó Ponsati, Agustí, Solà i Puig, Miquel, Pla i Quintana, Anna, Roglans i Ribas, Anna
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/16953
Acceso en línea:http://hdl.handle.net/10256/16953
Access Level:acceso abierto
Palabra clave:Compostos policíclics
Isomerització
Teoria del funcional de densitat
Polycyclic compounds
Isomerization
Density functionals
Descripción
Sumario:A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reac-tive cycloheptadiene, which concomitantly undergoes a regioselective [4+2] cycloaddition with alkenes. A complete mechanistic study of this transformation has been undertaken including DFT calculations. Overall, the methodology presented here constitutes a new and straightforward entry to polycyclic dihydroazepine and dihydrooxepine derivatives employing catalytic methods