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可见光驱动、铜催化的甘氨酸和肽的 C(sp )-H 脱羧烷基化反应。

Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp )-H Alkylation of Glycine and Peptides.

机构信息

Key Laboratory of Preclinical Study for New Drugs, of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000, China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, China.

出版信息

Angew Chem Int Ed Engl. 2018 Nov 26;57(48):15841-15846. doi: 10.1002/anie.201809400. Epub 2018 Nov 7.

Abstract

Despite a well-developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible-light-induced Cu-catalyzed decarboxylative C(sp )-H alkylation of glycine for preparing α-alkylated unnatural α-amino acids. It merits mentioning that the mild conditions and the good functional-group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical-radical coupling pathway is involved in the reaction.

摘要

尽管铜催化领域已经有了相当成熟和不断发展的研究工作,但铜作为光催化剂的潜力仍未得到充分探索。本文首次报道了可见光诱导的铜催化甘氨酸脱羧 C(sp 3 )-H 烷基化反应,用于制备α-取代的非天然α-氨基酸。值得一提的是,该反应条件温和,官能团容忍性好,可用于肽的修饰。通过机理研究表明,该反应涉及自由基-自由基偶联途径。

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