Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: Stereospecific synthesis of allenes

Herein we describe a robust and practical method to prepare enantiomerically enriched trisubstituted allenes using alkyl Grignard reagents and bench stable propargylic ammonium salts. Excellent yields as well as regio- and stereoselectivities are observed. Our conditions provide a solution to the al...

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Detalles Bibliográficos
Autores: Guisán-Ceinos, Manuel, Martín-Heras, Víctor, Soler-Yanes, Rita, Cárdenas Morales, Diego Jesús, Tortosa Manzanares, Mariola
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:10486/685378
Acceso en línea:http://hdl.handle.net/10486/685378
https://dx.doi.org/10.1039/c8cc03760d
Access Level:acceso abierto
Palabra clave:Grignard reagents
Ammonium salts
Racemization
Allenes
Copper-catalysed
Química
Descripción
Sumario:Herein we describe a robust and practical method to prepare enantiomerically enriched trisubstituted allenes using alkyl Grignard reagents and bench stable propargylic ammonium salts. Excellent yields as well as regio- and stereoselectivities are observed. Our conditions provide a solution to the allene racemization, which has been a long-standing problem when using Grignard reagents