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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.
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页码:9731 / 9738
页数:8
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