期刊
ACS CATALYSIS
卷 11, 期 13, 页码 8033-8041出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c00616
关键词
asymmetric catalysis; asymmetric transfer hydrogenation; manganese; aminobenzimidazole ligand; Mn hydride
资金
- National Natural Science Foundation of China [21773237, 21902166]
- Dalian National Laboratory for Clean Energy (DNL) Cooperation Fund, CAS [DNL201904]
A series of Mn(I) catalysts with chiral bidentate benzimidazoles derived from easily available amino acids have been developed for asymmetric transfer hydrogenation (ATH), showing high activity and enantioselectivity. These phosphine-free chiral Mn catalysts can efficiently convert bulky substrates into drug intermediate alcohols, with a possible mechanism and enantiocontrol model proposed based on experimental and DFT studies.
A series of Mn(I) catalysts with chiral bidentate benzimidazoles derived from easily available amino acids has been developed. These types of phosphine-free chiral Mn catalysts demonstrate high activity and enantioselectivity in asymmetric transfer hydrogenation (ATH) for a broad range of ketone substrates. A bulkier substrate, such as 2,6-dichloro-3-fluoroacetophenone, can be converted into the drug intermediate alcohol with up to 90% yield and 92% ee (e.g., crizotinib). On the basis of experimental and DFT studies, a possible mechanism for this Mn-catalyzed ATH is also proposed. DFT calculations further render a plausible model for enantiocontrol in ketone hydrogenation, in which the pi-pi stacking interaction between the catalyst and the substrate plays an important role.
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