Unnatural α-Amino Acid Synthesized through α-Alkylation of Glycine Derivatives by Diacyl Peroxides

被引：62

作者：

Tian, Hao ^{[1
]}

Xu, Wentao ^{[1
]}

Liu, Yuxiu ^{[1
]}

Wang, Qingmin ^{[1
,2
]}

机构：

[1] Nankai Univ, Coll Chem, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 13期

基金：

中国国家自然科学基金;

关键词：

C-H ALKYLATION; PEPTIDES; VINYLARENES; ALKYNES;

D O I：

10.1021/acs.orglett.0c01574

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a protocol for catalyst- and additive-free alpha-alkylation reactions of glycine derivatives with diacyl peroxides, which proceed by a pathway involving addition of alkyl radicals to imine intermediates. The diacyl peroxide substrate acts as both alkylation agent and oxidizing agent, which means it is atom-economical. It was applied to various glycine derivatives, dipeptides, and a 3,4-dihydroquinoxalin-2(1H)-one derivative and could be carried out on a gram scale, indicating its utility for late-stage functionalization.

引用

页码：5005 / 5008

页数：4

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