Copper-catalyzed asymmetric propargylation of imines enabled by a biphenol-based phosphoramidite ligand

Copper-catalyzed enantioselective propargylation of acyclic imines with electron-neutral protecting groups was established using a newly constructed phosphoramidite ligand, providing the corresponding homopropargyl amines in excellent yields and up to 95 : 5 er. The introduction of an ortho-substitu...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-09, Vol.10 (19), p.4935-4940
Main Authors: Qi-Qi, Yan, Cheng-Kai, Ruan, Yu-Qin, Deng, Yu-Chuan Pu, Wen-Dao Chu, Cheng-Yu, He, Quan-Zhong, Liu
Format: Article
Language:English
Subjects:
Amines
Catalysts
Copper
Enantiomers
Imines
Ligands
Organic chemistry
Protecting groups
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Summary:Copper-catalyzed enantioselective propargylation of acyclic imines with electron-neutral protecting groups was established using a newly constructed phosphoramidite ligand, providing the corresponding homopropargyl amines in excellent yields and up to 95 : 5 er. The introduction of an ortho-substituent and high electron deficiency of imines are proven to be the key for achieving high enantioselectivity. In addition, this protocol features an easy-to-handle copper(ii) catalyst and diverse downstream transformations.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo00871a