Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes

Condensation of BINAPO-(PhCHO)2 and 1,3,5- tris(4-aminophenyl)benzene (TAPB) results in a new imine-based chiral organic material (COM) that can be further postfunctionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show the necessary stabi...

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Detalles Bibliográficos
Autores: Sánchez de la Fuente, Miguel, López Magano, Alberto, Moya, Alicia, Mas Ballesté, Rubén
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/707715
Acceso en línea:http://hdl.handle.net/10486/707715
https://dx.doi.org/10.1021/acsami.3c04430
Access Level:acceso abierto
Palabra clave:Asymmetric catalysis
Organocatalysis
Chiral organic materials
Phosphine oxides
Aldol reaction
Química
Descripción
Sumario:Condensation of BINAPO-(PhCHO)2 and 1,3,5- tris(4-aminophenyl)benzene (TAPB) results in a new imine-based chiral organic material (COM) that can be further postfunctionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show the necessary stability to be used as a heterogeneous catalyst, the reduced amine-linked framework can be efficiently employed in asymmetric allylation of different aromatic aldehydes. Yields and enantiomeric excesses found are comparable to those observed for the molecular BINAP oxide catalyst, but importantly, the aminebased material also permits its recyclability