Catalytic Generation of Donor-Acceptor Cyclopropanes under N-Heterocyclic Carbene Activation and their Stereoselective Reaction with Alkylideneoxindoles

Formylcyclopropanes undergo activation in the presence of an N-heterocyclic carbene catalyst generating a donor-acceptor cyclopropane intermediate with the ability to undergo ring-opening followed by formal [4+2] cycloaddition with alkylideneoxindoles. This enables the direct enantio- and diastereos...

Descripción completa

Detalles Bibliográficos
Autores: Prieto Aretxabaleta, Liher, Sánchez Díez, Eduardo, Uria Pujana, Uxue, Reyes Martín, Efraim, Carrillo Fernández, María Luisa, Vicario Hernando, José Luis
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/64341
Acceso en línea:http://hdl.handle.net/10810/64341
Access Level:acceso abierto
Palabra clave:asymmetric catalysis
cycloaddition
cyclopropanes
N-heterocyclic carbenes
Descripción
Sumario:Formylcyclopropanes undergo activation in the presence of an N-heterocyclic carbene catalyst generating a donor-acceptor cyclopropane intermediate with the ability to undergo ring-opening followed by formal [4+2] cycloaddition with alkylideneoxindoles. This enables the direct enantio- and diastereoselective synthesis of tetrahydropyrano[ 2,3-b]indoles through the use of a chiral NHC catalyst. Keywords: asymmetric