C1-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model

C1-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model

A family of ferrocene-based chiral PNP ligands is reported. These tridentate ligands were successfully applied in Mn-catalyzed asymmetric hydrogenation of ketones, giving high enantioselectivities (92%∼99% ee for aryl alkyl ketones) as well as high efficiencies (TON up to 2000). In addition, dialkyl...

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Bibliographic Details
Published in:ACS catalysis Vol. 10; no. 23; pp. 13794 - 13799
Main Authors: Zeng, Liyao, Yang, Huaxin, Zhao, Menglong, Wen, Jialin, Tucker, James H. R, Zhang, Xumu
Format: Journal Article
Language:English
Published: American Chemical Society 04-12-2020
Subjects:
ketone
enantioinduction model
manganese
PNP ligand
asymmetric hydrogenation
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Summary:A family of ferrocene-based chiral PNP ligands is reported. These tridentate ligands were successfully applied in Mn-catalyzed asymmetric hydrogenation of ketones, giving high enantioselectivities (92%∼99% ee for aryl alkyl ketones) as well as high efficiencies (TON up to 2000). In addition, dialkyl ketones could also be hydrogenated smoothly. Manganese intermediates that might be involved in the catalytic cycle were analyzed. DFT calculation was carried out to help understand the chiral induction model. The Mn/PNP catalyst could discriminate two groups with different steric properties by deformation of the phosphine moiety in the flexible 5-membered ring.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.0c04206