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Unnatural α-Amino Acid Synthesized through α-Alkylation of Glycine Derivatives by Diacyl Peroxides.
Organic Letters ( IF 5.2 ) Pub Date : 2020-06-17 , DOI: 10.1021/acs.orglett.0c01574
Hao Tian 1 , Wentao Xu 1 , Yuxiu Liu 1 , Qingmin Wang 1, 2
Affiliation  

We have developed a protocol for catalyst- and additive-free α-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.

中文翻译:

通过二酰基过氧化物将甘氨酸衍生物进行α-烷基化反应合成的非天然α-氨基酸。

我们已经开发出用于甘氨酸衍生物与二酰基过氧化物的无催化剂和无添加剂的α-烷基化反应的方案,该方案通过涉及将烷基自由基加成至亚胺中间体的途径进行。过氧化二酰基的底物既充当烷基化剂又充当氧化剂,这意味着它是原子经济的。它已应用于各种甘氨酸衍生物,二肽和3,4-二氢喹喔啉-2(1 H)-one衍生物,并且可以克量进行,表明其可用于后期功能化。
更新日期:2020-07-02
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