Brønsted acid versus phase-transfer catalysis in the enantioselective transannular aminohalogenation of enesultams

We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium-sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase-transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enant...

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Detalles Bibliográficos
Autores: Luis-Barrera, Javier, Rodriguez, Sandra, Uria, Uxue, Reyes, Efraim, Prieto, Liher, Carrillo, Luisa, Pedrón, Manuel, Tejero, Tomás, Merino, Pedro, Vicario, Jose L.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/303535
Acceso en línea:http://hdl.handle.net/10261/303535
Access Level:acceso abierto
Descripción
Sumario:We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium-sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase-transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enantioselectivities. The mechanism of the reaction was also studied by using computational tools; we observed that the reaction involves the participation of a conformer of the nine-membered cyclic substrate with planar chirality in which the stereochemical outcome is controlled by the relative reactivity of the two pseudorotational enantiomers when interacting with the chiral catalyst.

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