Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts

The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral N , N , P -ligands. This method features a broad substrate scope and wide functional group tolerance, generating...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-05, Vol.57 (38), p.4674-4677
Main Authors: Huang, Jian, Kong, Han-Han, Li, Si-Jia, Zhang, Rui-Jin, Qian, Hao-Dong, Li, Dan-Ran, He, Jin-Yu, Zheng, Yi-Nuo, Xu, Hao
Format: Article
Language:English
Subjects:
Amines
Copper
Crystallography
Enantiomers
Esters
Functional groups
NMR
Nuclear magnetic resonance
Substrates
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Summary:The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral N , N , P -ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals. A highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized under mild conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc00663k