Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides

A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2021-11, Vol.23 (23), p.9549-9553
Main Authors: Xin, Hong, Yuan, Zi-Hang, Yang, Mingyu, Wang, Ming-Hua, Duan, Xin-Hua, Guo, Li-Na
Format: Article
Language:English
Subjects:
Amino acids
Carbonyl compounds
Carbonyl groups
Carbonyls
Glycine
Green chemistry
Peptides
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Summary:A metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides a straightforward route to unnatural amino acids bearing a distal carbonyl group with moderate to good yields. Preliminary mechanistic studies revealed that both a SET event and radical chain propagation were involved in this transformation. A metal free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.
ISSN:1463-9262
1463-9270
DOI:10.1039/d1gc03230e