Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals

A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as...

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Detalles Bibliográficos
Autores: Mellado Hidalgo, Miguel, Romero Cavagnaro, Elias A., Nageswaran, Sajanthanaa, Puddu, Sabrina, Kennington, Stuart C. D., Costa i Arnau, Anna M., Romea, Pedro, Urpí Tubella, Fèlix, Aullón López, Gabriel, Font Bardia, Ma. Mercedes
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2023
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:2445/196206
Acceso en línea:https://hdl.handle.net/2445/196206
Access Level:acceso abierto
Palabra clave:Aldehids
Estructura molecular
Aldehydes
Molecular structure
Descripción
Sumario:A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon-carbon bond-forming reactions, can be smoothly removed to give access to a variety of enantiomerically pure compounds with high synthetic value.

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