Dual Photoredox and Copper-Catalyzed Asymmetric Remote C(sp3)–H Alkylation of Hydroxamic Acid Derivatives with Glycine Derivatives

Dual photoredox and copper-catalyzed remote asymmetric C­(sp)3–H alkylation of hydroxamic acid derivatives with glycine derivatives via a 1,5-hydrogen transfer (1,5-HAT) process has been realized. The reaction was characterized by redox-neutral and mild conditions, good yields, excellent enantiosele...

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Published inJournal of organic chemistry Vol. 90; no. 3; pp. 1219 - 1232
Main Authors Chen, Jian, Ruan, Pingping, Fan, Hongying, Zhang, Xue, He, Shiyun, Hou, Jinyu, Ye, Meiling, Li, Yuanyuan, Lv, Guanghui, Wu, Yong
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 24.01.2025
Subjects
alkylation
dipeptides
enantioselectivity
organic chemistry
redox reactions
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Summary:Dual photoredox and copper-catalyzed remote asymmetric C­(sp)3–H alkylation of hydroxamic acid derivatives with glycine derivatives via a 1,5-hydrogen transfer (1,5-HAT) process has been realized. The reaction was characterized by redox-neutral and mild conditions, good yields, excellent enantioselectivity, and broad substrate scope. This protocol provides a straightforward and efficient strategy to prepare highly valuable enantioenriched noncanonical α-amino acids. Moreover, the potential synthetic value of this reaction was demonstrated in late-stage asymmetric alkylation of dipeptides with a high diastereomeric ratio.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01677