Reaction Rates of Various N-Acylenamines in the Inverse-Electron-Demand Diels-Alder Reaction

被引：4

作者：

Engelsma, Sander B. ^{[1
]}

van den Ende, Thomas C. ^{[1
]}

Overkleeft, Hermen S. ^{[1
]}

van der Marel, Gijsbert A. ^{[1
]}

Filippov, Dmitri V. ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, Dept Bioorgan Synth, Einsteinweg 55, NL-2333 CC Leiden, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 20-21期

关键词：

Diels-Alder reaction; Tetrazine; Reaction rates; Cycloaddition; N-Acylenamines; 1,2,4,5-TETRAZINE;

D O I：

10.1002/ejoc.201800094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In light of the bioorthogonal inverse-electron-demand Diels-Alder strategy, an extended investigation into the effects of ring strain and electron inductive effects on the reactivity of the N-acylenamine core towards tetrazine has been carried out. Through a comparative study between N-acylazetines, N-vinylcarbamates and an N-vinylamide it was shown that ring strain has a more significant effect on reaction rate than electron donation. A significantly improved synthetic route is reported for the preparation of an N-acylazetine biorthogonal tag we have invented previously.

引用

页码：2587 / 2591

页数：5

共 16 条

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