Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide

An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one‐pot synthesis of tetrahydroquinoxalines was also developed starting directly from α‐ketoaldehydes and 1,2‐diaminobenzene. Formic acid was used as a safe and e...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-09, Vol.55 (39), p.12083-12087
Main Authors: Yang, Peng, Lim, Li Hui, Chuanprasit, Pratanphorn, Hirao, Hajime, Zhou, Jianrong (Steve)
Format: Article
Language:English
Subjects:
Amination
Amines
Catalysts
chiral alkylamines
Decarboxylation
Enantiomers
Formic acid
Ketones
Nickel
Organic compounds
reductive amination
Stereoselectivity
synthetic methods
transfer hydrogenation
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Summary:An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one‐pot synthesis of tetrahydroquinoxalines was also developed starting directly from α‐ketoaldehydes and 1,2‐diaminobenzene. Formic acid was used as a safe and economic surrogate for high‐pressure hydrogen gas. Strongly σ‐donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate. Reducing costs: Reductive amination of ketones with both arylamines and benzhydrazide was realized in the presence of catalysts based on nickel rather than expensive noble metals. Formic acid was used as a safe and cheap surrogate for high‐pressure hydrogen gas.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606821