Synthesis of α-chiral amides via synergistic visible-light-induced Wolff rearrangement and asymmetric NHC catalysis

Herein, a visible-light-induced chiral N-heterocyclic carbene (NHC)-catalyzed asymmetric amination of ketenes has been developed. This strategy provides a convenient and facile synthetic protocol for the efficient construction of α-chiral amides under mild reaction conditions with moderate to excell...

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Bibliographic Details
Published inNew journal of chemistry Vol. 48; no. 35; pp. 15287 - 15291
Main Authors Wang, Jiaomei, Chen, Yangxu, Miao, Siyan, Yao, Changsheng, Zhang, Kai
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 09.09.2024
Subjects
Amides
Asymmetry
Chemical synthesis
Ketenes
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Summary:Herein, a visible-light-induced chiral N-heterocyclic carbene (NHC)-catalyzed asymmetric amination of ketenes has been developed. This strategy provides a convenient and facile synthetic protocol for the efficient construction of α-chiral amides under mild reaction conditions with moderate to excellent yields and stereoselectivities (up to 95% yields and 97 : 3 e.r.). Furthermore, a chiral 2-phenyl-1-propylamine derivative and ( R )-ibuprofen could be obtained after simple transformations of the chiral products.
ISSN:1144-0546
1369-9261
DOI:10.1039/D4NJ03410D