Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey

The recent development of asymmetric organocatalytic C-C bond forming reactions involving organoboranes has attracted big interest in the synthetic community. Asymmetric organocatalytic additions to enones, aldehydes, ketones, imines, dienes, and related systems can be carried out with different org...

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Detalles Bibliográficos
Autores: Simonetti, Sebastián Osvaldo, Pellegrinet, Silvina Carla
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2019
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/106179
Acceso en línea:http://hdl.handle.net/11336/106179
Access Level:acceso abierto
Palabra clave:ASYMMETRIC SYNTHESIS
DENSITY FUNCTIONAL CALCULATIONS
ORGANOBORON COMPOUNDS
ORGANOCATALYSIS
REACTION MECHANISMS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:The recent development of asymmetric organocatalytic C-C bond forming reactions involving organoboranes has attracted big interest in the synthetic community. Asymmetric organocatalytic additions to enones, aldehydes, ketones, imines, dienes, and related systems can be carried out with different organoboron compounds (boronic acids and esters and trifluoroborate salts) to give products with very good yields and enantiomeric ratios. In particular, many BINOL and α-hydroxyacid derivatives have been used as chiral organocatalysts. In this review, we describe the mechanisms that have been proposed based on theoretical and experimental studies for asymmetric organocatalytic C-C bond forming reactions with organoboron compounds. The mechanistic understanding that has been gained should contribute to the progress of this promising area of organic chemistry.