Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines.

The iridium-catalyzed asym. hydrogenation of several N-sulfonyl allyl amines was reported. All substrates could be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The com. available threonine-derived phosphinite (UbaPHOX) iridium complex had been found to...

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Detalles Bibliográficos
Autores: Cabré Montesinos, Albert, Verdaguer i Espaulella, Xavier, Riera i Escalé, Antoni
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:2445/143362
Acceso en línea:https://hdl.handle.net/2445/143362
Access Level:acceso abierto
Palabra clave:Iridi
Catàlisi asimètrica
Hidrogenació
Síntesi de fàrmacs
Iridium
Enantioselective catalysis
Hydrogenation
Drug synthesis
Descripción
Sumario:The iridium-catalyzed asym. hydrogenation of several N-sulfonyl allyl amines was reported. All substrates could be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The com. available threonine-derived phosphinite (UbaPHOX) iridium complex had been found to be the best catalyst for this catalytic application, affording β-Me amines I [R1 = H, 4-Cl, 4-Br, etc.;R2 = Me, i-Pr, 4-MeC6H4; R3 = H, Me] with good to excellent ee values (up to 94%). The synthetic potential of this novel methodol. was demonstrated by the formal synthesis of Lorcaserin and LY-404187.