Rhodium-Catalyzed Formal C-O Insertion in Carbene/Alkyne Metathesis Reactions: Synthesis of 3-Substituted 3H-Indol-3-ols

被引：14

作者：

Jia, Shikun ^{[1
]}

Dong, Guizhi ^{[1
]}

Ao, Chaoqun ^{[1
]}

Jiang, Xianxing ^{[1
]}

Hu, Wenhao ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 11期

基金：

中国博士后科学基金;

关键词：

CHEMOSELECTIVE OXIDATIVE AMINATION; N-H INSERTION; ASYMMETRIC-SYNTHESIS; CARBENES; ALKYNES; ACCESS; CYCLOADDITION; REACTIVITY; FUNCTIONALIZATION; TRANSANNULATION;

D O I：

10.1021/acs.orglett.9b01492

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and novel rhodium-catalyzed formal C-O insertion reaction of alkyne-tethered diazo compounds for the synthesis of 3H-indol-3-ols is described. A type of donor/donor rhodium carbene generated in situ via a carbene/alkyne metathesis (CAM) process is the key intermediate and terminates in a unique transformation different from donor/acceptor carbenoids. In addition, O-18-labeling experiments indicate that intramolecular oxygen-atom transfer from the amide group to the carbon-carbon triple bond occurs during this transformation.

引用

收藏

页码：4322 / 4326

页数：5

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