Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins

Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reac...

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Detalles Bibliográficos
Autores: Bonilla, Pablo, Rey, Yannick P., Holden, Catherine M., Melchiorre, Paolo
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
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:2072/350698
Acceso en línea:http://hdl.handle.net/2072/350698
https://doi.org/10.1002/anie.201808183
Access Level:acceso abierto
Palabra clave:54
Descripción
Sumario:Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reactivity of chiral iminium ions to trigger radical cascade reactions with high enantioselectivity. By combining two sequential radical- based bond-forming events, the method converts unactivated olefins and a,b-unsaturated aldehydes into chiral adducts in a single step. The implementation of an asymmetric three- component radical cascade further demonstrates the complex- ity-generating power of this photochemical strategy.