Substrate Controlled Product Divergence in CO2 Conversion to Heterocyclic Products

Substituted epoxy alcohols and amines allow for substrate- controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach allows for an unusual scope of CO2 derived products by initial activation of CO2 through the amine or alcoho...

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Detalles Bibliográficos
Autores: Rintjema, Jeroen, Epping, Roel, Fiorani, Giulia, Martín, Eddy, Escudero-Adán, Eduardo C., Kleij, Arjan W.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
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:2072/356060
Acceso en línea:http://hdl.handle.net/2072/356060
https://doi.org/10.1002/anie.201511521
Access Level:acceso abierto
Palabra clave:54
Descripción
Sumario:Substituted epoxy alcohols and amines allow for substrate- controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach allows for an unusual scope of CO2 derived products by initial activation of CO2 through the amine or alcohol unit, providing nucleophiles for intramolecular epoxy ring-opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile assisted ring-opening step following an SNi pathway and a 5-exo-tet cyclization leading towards heterocyclic scaffolds.