Light-triggered Enantioselective Organocatalytic Mannich-type Reaction

<div> <p> Abstract</p> <p> Disclosed herein is a photochemical organocatalytic strategy for the direct enantioselective Mannich-type reaction of 2-alkyl-benzophenones and cyclic imines. The chemistry exploits the light-triggered enolization of 2-alkyl-benzophenones to generat...

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Detalles Bibliográficos
Autores: Hepburn, Hamish B., Magagnano, Giandomenico, Melchiorre, Paolo
Tipo de recurso: artículo
Fecha de publicación:2016
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:2072/305755
Acceso en línea:http://hdl.handle.net/2072/305755
https://doi.org/10.1055/s-0036-1588606
Access Level:acceso abierto
Palabra clave:enantioselective catalysis
organocatalysis
Mannich-type reaction
photochemistry
synthetic methods
Descripción
Sumario:<div> <p> Abstract</p> <p> Disclosed herein is a photochemical organocatalytic strategy for the direct enantioselective Mannich-type reaction of 2-alkyl-benzophenones and cyclic imines. The chemistry exploits the light-triggered enolization of 2-alkyl-benzophenones to generate transient hydroxy-<em>o</em>-quinodinomethanes. These fleeting intermediates can be stereoselectively intercepted by imines upon activation with a chiral organic catalyst, derived from natural cinchona alkaloids. The developed method uses mild conditions, simple sources of illumination and easily available substrates and catalysts, affording enantioenriched chiral amines that are difficult to synthesize by other approaches.</p> </div> <p> &nbsp;</p>