Chinese Journal of Organic Chemistry >
Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines
Received date: 2023-04-17
Revised date: 2023-06-16
Online published: 2023-07-13
Supported by
National Natural Science Foundation of China(22078045); National Natural Science Foundation of China(21176039)
A visible-light-mediated decarboxylative radical alkylation of glyoxylimines for preparing α-alkylated unnatural amino acid derivatives was developed. Various alkyl radicals generated by tetrachloro-N-hydroxyphthalimide (TCNHPI) active esters were added to imines in good yields under visible light irradiation. Iridium complex was selected as photocatalyst and also, Hantzsch ester (HE) as hydrogen transfer reagent was essential. Fluoboric acid (HBF4) significantly improved the yield. Mild reaction conditions showed wide substrate scopes. In addition, the straightforward and efficient one-pot procotol, involved a multicomponent reaction of ethyl glyoxalate, primary amine and TCNHPI active ester occurred smoothly. This scheme provides a new method for the synthesis of α-alkylated unnatural amino acid derivatives.
Yongling Wang , Tiexin Zhang , Xuming Zhang , Hanyang Sun , Jinyao Leng , Yaming Li . Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines[J]. Chinese Journal of Organic Chemistry, 2023 , 43(12) : 4284 -4293 . DOI: 10.6023/cjoc202304020
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