Synthesis of C4-Aminated Indoles via a Catellani and Retro-Diels-Alder Strategy

被引：72

作者：

Zhang, Bo-Sheng ^{[1
]}

Li, Yuke ^{[2
,3
]}

Zhang, Zhe ^{[1
]}

An, Yang ^{[1
]}

Wen, Yu-Hua ^{[1
]}

Gou, Xue-Ya ^{[1
]}

Quan, Si-Qi ^{[1
]}

Wang, Xin-Gang ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[3] Chinese Univ Hong Kong, Ctr Sci Modeling & Computat, Shatin, Hong Kong, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 24期

基金：

中国国家自然科学基金;

关键词：

C-H ARYLATION; TETRASUBSTITUTED HELICAL ALKENES; PALLADIUM-CATALYZED ANNULATION; REGIOSELECTIVE SYNTHESIS; FUNCTIONALIZATION; ACTIVATION; ROUTE; PD/NORBORNENE; AMIDATION;

D O I：

10.1021/jacs.9b05009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly functionalized 4-aminoindoles were synthesized via the three-component cross-coupling of o-iodoaniline, N-benzoyloxyamines, and norbornadiene. The Catellani and retro-Diels-Alder strategy was used in this domino process. o-Iodoaniline, with electron-donating and sterically hindered protecting groups, made the reaction selective toward o-C-H amination. On the basis of density functional theory calculations, the intramolecular Buchwald coupling of this reaction underwent a dearomatization and a 1,3-palladium migration process. The reasons for the control of the chemical selectivity by the protecting groups are given. Moreover, synthetic applications toward 4-piperazinylindole and a GOT1 inhibitor were realized.

引用

页码：9731 / 9738

页数：8

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