Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl] , 39 ketones including aromatic, he...

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Published inOrganic letters Vol. 24; no. 1; pp. 415 - 419
Main Authors Zhang, Lin, Zhang, Ling, Chen, Qian, Li, Linlin, Jiang, Jian, Sun, Hao, Zhao, Chong, Yang, Yuanyong, Li, Chun
Format Journal Article
LanguageEnglish
Published United States 14.01.2022
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Summary:Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl] , 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04101