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...
| Autores: | , , , |
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| 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 |
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oai:repositorio.uam.es:10486/707715 |
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España |
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Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes Sánchez de la Fuente, Miguel López Magano, Alberto Moya, Alicia Mas Ballesté, Rubén Asymmetric catalysis Organocatalysis Chiral organic materials Phosphine oxides Aldol reaction Química 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 Financial support was provided by the Spanish Government (PID2019-110637RB-I00). A.L.-M. thanks UAM for a FPIUAM predoctoral fellowship. M.S.-F. thanks Ministerio de Ciencia e Innovación for a FPI contract (PRE2020-092295). A.M. acknowledges the Spanish Government and the European Union through the Funds Next Generation through grant Maria Zambrano-UAM (CA3/RSUE/2021-00648) American Chemical Society http://hdl.handle.net/10486/707715 https://dx.doi.org/10.1021/acsami.3c04430 |
| title |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes |
| spellingShingle |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes Sánchez de la Fuente, Miguel Asymmetric catalysis Organocatalysis Chiral organic materials Phosphine oxides Aldol reaction Química |
| title_short |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes |
| title_full |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes |
| title_fullStr |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes |
| title_full_unstemmed |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes |
| title_sort |
Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes |
| author |
Sánchez de la Fuente, Miguel |
| author_facet |
Sánchez de la Fuente, Miguel López Magano, Alberto Moya, Alicia Mas Ballesté, Rubén |
| author_role |
author |
| author2 |
López Magano, Alberto Moya, Alicia Mas Ballesté, Rubén |
| author2_role |
author author author |
| topic |
Asymmetric catalysis Organocatalysis Chiral organic materials Phosphine oxides Aldol reaction Química |
| topic_facet |
Asymmetric catalysis Organocatalysis Chiral organic materials Phosphine oxides Aldol reaction Química |
| description |
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 |
| publishDate |
2023 |
| format |
article |
| url |
http://hdl.handle.net/10486/707715 https://dx.doi.org/10.1021/acsami.3c04430 |
| language |
eng |
| eu_rights_str_mv |
openAccess |
| publisher |
American Chemical Society |
| institution |
Universidad Autónoma de Madrid |
| collection |
Biblos-e Archivo. Repositorio Institucional de la UAM |
| reponame_str |
Biblos-e Archivo. Repositorio Institucional de la UAM |
| instname_str |
Universidad Autónoma de Madrid |
| _version_ |
1878436753884315649 |
| publishDateSort |
2023 |
| author_browse |
López Magano, Alberto Mas Ballesté, Rubén Moya, Alicia Sánchez de la Fuente, Miguel |
| publisherStr |
American Chemical Society |
| score |
6,9303427 |