Catalytic Enantioselective Dearomatization/Rearomatization of 2-Nitroindoles to Access 3-Indolyl-3′-Aryl-/Alkyloxindoles: Application in the Formal Synthesis of Cyclotryptamine Alkaloids

被引:24
作者
Yuan, Wei-Cheng [1 ]
Zhou, Xiao-Jian [2 ]
Zhao, Jian-Qiang [1 ]
Chen, Yong-Zheng [2 ]
You, Yong [1 ]
Wang, Zhen-Hua [1 ]
机构
[1] Chengdu Univ, Inst Adv Study, Chengdu 610106, Peoples R China
[2] Zunyi Med Univ, Gener Drug Res Ctr Guizhou Prov, Sch Pharm, Key Lab Biocatalysis & Chiral Drug Synth Guizhou, Zunyi 563006, Guizhou, Peoples R China
关键词
DEAROMATIVE 3+2 CYCLOADDITION; CONCISE TOTAL-SYNTHESIS; CASCADE REACTION; 3-ISOTHIOCYANATO OXINDOLES; 3-SUBSTITUTED OXINDOLES; ASYMMETRIC-SYNTHESIS; 3-NITROINDOLES; CONSTRUCTION; 2-NITROBENZOFURANS; TERTIARY;
D O I
10.1021/acs.orglett.0c02350
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first catalytic enantioselective dearomatization/rearomatization of 2-nitroindoles triggered by the Michael addition of 3-monosubstituted oxindoles was established. A wide range of 3-indolyl-3 '-alkyloxindoles (up to 99% yield, 97% ee) and 3-indolyl-3 '-aryloxindoles (up to 95% yield, 99% ee) were obtained by using an organocatalyst. This method provides an unprecedented strategy to access structurally diverse 3,3 '-disubstituted oxindoles bearing a sterically congested triaryl-containing all-carbon quaternary stereocenter. The utility of this approach was verified by the formal synthesis of cyclotryptamine alkaloids.
引用
收藏
页码:7088 / 7093
页数:6
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