Self‐Assembly of a Chiral Bis‐phosphine Ligand Bearing Pyridyl Crown Ethers and Chiral Primary Ammoniums: Application to Catalytic Asymmetric Hydrogenation Reactions

A chiral bis‐hosphine ligand bearing two pyridyl crown ethers was complexed with primary ammonium salts of different absolute configuration to form supramolecular chiral catalysts, which were successfully applied in the Rh‐catalyzed asymmetric hydrogenation of α‐dehydroamino acid esters and Ir‐catal...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2022-05, Vol.7 (20), p.n/a
Main Authors: Lu, Ying‐Bo, Chen, Chuan‐Fu, Hu, Yi‐Hu, Zhang, Xi‐Chang, Fang, Qiang, Yang, Li‐Yao, Xie, Lin‐Jie, Wu, Jing, Li, Shijun
Format: Article
Language:English
Subjects:
asymmetric catalysis
crown ethers
host-guest chemistry
self-assembly
supramolecular catalysts
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Summary:A chiral bis‐hosphine ligand bearing two pyridyl crown ethers was complexed with primary ammonium salts of different absolute configuration to form supramolecular chiral catalysts, which were successfully applied in the Rh‐catalyzed asymmetric hydrogenation of α‐dehydroamino acid esters and Ir‐catalyzed asymmetric hydrogenation of quinoxalines. By comparison with the non‐assembled catalysts, the complexation between the chiral catalysts and primary ammoniums obviously improved enantioselectivities. Up to 11 % enhancement in ee values in asymmetric hydrogenation of α‐dehydroamino acid esters and 30 % enhancement in ee values in asymmetric hydrogenation of quinoxalines were achieved. A bis‐phosphine ligand bearing pyridyl crown ethers was applied to the asymmetric hydrogenation of α‐dehydroamino acid esters and quinoxaline derivatives, in which the presence of primary ammonium salts as guests could significantly improve the enantioselectivities.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202200912