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
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
收藏
页码:9731 / 9738
页数:8
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