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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 18期

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

页码：7088 / 7093

页数：6

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