Asymmetric synthesis of Rauhut-Currier-type esters via Mukaiyama-Michael reaction to acylphosphonates under bifunctional catalysis

A highly enantioselective organocatalytic Mukaiyama-Michael reaction of silyloxy dienes and α,β-unsaturated acyl phosphonates under bifunctional organocatalysis is presented. The new reactivity triggered by the catalyst conducted to Rauhut-Currier type esters, via a formal conjugate addition to α,β-...

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Detalles Bibliográficos
Autores: Laina-Martín, Víctor, Del Río-Rodríguez, Roberto, Díaz-Tendero Victoria, Sergio, Fernández-Salas, Jose A., Alemán Lara, José Julián
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/687223
Acceso en línea:http://hdl.handle.net/10486/687223
https://dx.doi.org/10.1039/c8cc07561a
Access Level:acceso abierto
Palabra clave:Asymmetric synthesis
Catalysis
Chemical structure
Chemical parameters
Chromatography
Enantioselectivity
Regioselectivity
Mukaiyama Michael reaction
Química
Descripción
Sumario:A highly enantioselective organocatalytic Mukaiyama-Michael reaction of silyloxy dienes and α,β-unsaturated acyl phosphonates under bifunctional organocatalysis is presented. The new reactivity triggered by the catalyst conducted to Rauhut-Currier type esters, via a formal conjugate addition to α,β-unsaturated esters. This protocol proceeds under mild conditions with complete regioselectivity and excellent enantiocontrol