Rhodium-Catalyzed Intermolecular Stereoselective Allylation of Indoles with Allenes

被引：13

作者：

Ma, Chaoyan ^{[1
]}

Li, Can ^{[2
]}

Bai, Jiahui ^{[2
]}

Xiao, Junzhe ^{[2
]}

Zhai, Yizhan ^{[2
]}

Guo, Yinlong ^{[2
]}

Ma, Shengming ^{[2
,3
,4
]}

机构：

[1] Zhejiang Univ, Ctr Chem Frontier Technol, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[3] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

[4] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, Shanghai 200433, Peoples R China

来源：

ACS CATALYSIS | 2022年 / 12卷 / 16期

基金：

国家重点研发计划;

关键词：

indoles; allenes; allylation; rhodium-catalysis; chirality transfer; Z-selectivity; C-H ALLYLATION; FUNCTIONALIZATION; ALCOHOLS; ACCESS;

D O I：

10.1021/acscatal.2c01433

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A rhodium-catalyzed C-H functionalization-based intermolecular allylation of indoles with trisubstituted allenes has been developed. This synthetic process proceeds with an excellent regioselectivity, Z-selectivity, high efficiency of chirality transfer, and a wide tolerance of reactive functional groups under mild conditions. Late-stage modification on a series of complex bioactive or drug molecules and various synthetic transformations has been demonstrated. A reaction mechanism has been proposed on the basis of mechanistic experiments and SAESI-MS studies.

引用

页码：10141 / 10146

页数：6

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