Direct and asymmetric nickel(II)-catalyzed construction of carbon−carbon bonds from N‑acyl thiazinanethiones

A wide array of new N-acyl thiazinanethiones are employed in a number of direct and enantioselective carbon-carbon bond forming reactions catalyzed by nickel(II) complexes. The electrophilic species are mostly prepared in situ from ortho esters, methyl ethers, acetals, and ketals, which makes the ov...

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Detalles Bibliográficos
Autores: Kennington, Stuart C. D., Taylor, Adam J., Romea, Pedro, Urpí Tubella, Fèlix, Aullón López, Gabriel, Font Bardia, Ma. Mercedes, Ferré, Laura, Rodrigálvarez García, Jesús
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
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:2445/127694
Acceso en línea:https://hdl.handle.net/2445/127694
Access Level:acceso abierto
Palabra clave:Catàlisi
Níquel
Catalysis
Nickel
Descripción
Sumario:A wide array of new N-acyl thiazinanethiones are employed in a number of direct and enantioselective carbon-carbon bond forming reactions catalyzed by nickel(II) complexes. The electrophilic species are mostly prepared in situ from ortho esters, methyl ethers, acetals, and ketals, which makes the overall process highly efficient and experimentally straightforward. Theoretical calculations indicate that the reactions pro-ceed through an open transition state in a SN1-like mechanism. The utility of this novel procedure has been demonstrated by the asymmetric preparation of syntheti-cally useful intermediates and the total synthesis of pe-peromin D.