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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Published in:ACS catalysis 2020-12, Vol.10 (23), p.13794-13799
Main Authors: Zeng, Liyao, Yang, Huaxin, Zhao, Menglong, Wen, Jialin, Tucker, James H. R, Zhang, Xumu
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cited_by cdi_FETCH-LOGICAL-a280t-3ace865cc443c2c1bcba50280aff0cf995f974e3d551f05fd7f306f91a67b1103
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container_end_page 13799
container_issue 23
container_start_page 13794
container_title ACS catalysis
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creator Zeng, Liyao
Yang, Huaxin
Zhao, Menglong
Wen, Jialin
Tucker, James H. R
Zhang, Xumu
description 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.
doi_str_mv 10.1021/acscatal.0c04206
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title C1-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model
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