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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| Published in | New journal of chemistry Vol. 48; no. 35; pp. 15287 - 15291 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Cambridge
Royal Society of Chemistry
09.09.2024
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Wang, Jiaomei Miao, Siyan Yao, Changsheng Chen, Yangxu Zhang, Kai |
| Author_xml | – sequence: 1 givenname: Jiaomei surname: Wang fullname: Wang, Jiaomei organization: School of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou 221018, P. R. China – sequence: 2 givenname: Yangxu surname: Chen fullname: Chen, Yangxu organization: Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China – sequence: 3 givenname: Siyan surname: Miao fullname: Miao, Siyan organization: Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China – sequence: 4 givenname: Changsheng orcidid: 0000-0002-0185-2366 surname: Yao fullname: Yao, Changsheng organization: Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China – sequence: 5 givenname: Kai orcidid: 0000-0001-9341-0444 surname: Zhang fullname: Zhang, Kai organization: Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China |
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| Title | Synthesis of α-chiral amides via synergistic visible-light-induced Wolff rearrangement and asymmetric NHC catalysis |
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