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

Autor: Sánchez-Fuente M; Department of Inorganic Chemistry (Module 7), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., López-Magano A; Department of Inorganic Chemistry (Module 7), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Moya A; Department of Inorganic Chemistry (Module 7), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Mas-Ballesté R; Department of Inorganic Chemistry (Module 7), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.; Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain.
Jazyk: angličtina
Zdroj: ACS applied materials & interfaces [ACS Appl Mater Interfaces] 2023 Jun 28; Vol. 15 (25), pp. 30212-30219. Date of Electronic Publication: 2023 Jun 12.
DOI: 10.1021/acsami.3c04430
Abstrakt: 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 post-functionalized 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 amine-based material also permits its recyclability.
Databáze: MEDLINE