Asymmetric Stepwise Reductive Amination of Aryl N‐Heteroaryl Ketones with Benzyl Amines via Iridium Catalysis

An asymmetric reductive amination of aryl N‐heteroaryl ketones with Benzyl Amines has been realized via one‐pot two‐step process, using p‐toluenesulfonic acid and chiral iridium complexes as catalysts, a mixture of formic acid/triethylamine as a reductant. Twenty‐three examples of chiral aryl N‐hete...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-11, Vol.10 (11), p.2950-2953
Main Authors: Yang, Bing, Fu, Hao, Yuan, Jing, Wen, Simiaomiao, Wang, Chunqin, Liu, Qixing, Zhou, Haifeng
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Aryl N-heteroaryl methylamines
Asymmetric reductive amination
Asymmetry
Catalysis
Enantioselectivity
Formic acid
Iridium
Iridium compounds
Ketones
Organic chemistry
Reducing agents
Triethylamine
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Summary:An asymmetric reductive amination of aryl N‐heteroaryl ketones with Benzyl Amines has been realized via one‐pot two‐step process, using p‐toluenesulfonic acid and chiral iridium complexes as catalysts, a mixture of formic acid/triethylamine as a reductant. Twenty‐three examples of chiral aryl N‐heteroaryl methylamines were obtained with good yields and up to 99% ee. Various chiral aryl N‐heteroaryl methylamines were prepared with good yields and up to 99% enantioselectivity via one‐pot stepwise ketimine formation/asymmetric transfer hydrogenation of aryl N‐heteroaryl ketones and benzyl amines.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100472