Highly Chemo- and Stereoselective Catalyst-Controlled Allylic C-H Insertion and Cyclopropanation Using Donor/Donor Carbenes

被引：83
|
作者：
Zhu, Dong [1 ]
Chen, Lianfen [1 ]
Zhang, He [1 ]
Ma, Zhiqiang [1 ]
Jiang, Huanfeng [1 ]
Zhu, Shifa [1 ]
机构：
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 38期
关键词：
asymmetric catalysis; carbenes; cyclopropanation; heterocycles; ruthenium; ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION; CHIRAL DIRHODIUM(II) CATALYSTS; ALPHA-DIAZOCARBONYL COMPOUNDS; METAL CARBENE; ASYMMETRIC-SYNTHESIS; MIGRATORY INSERTION; PROPARGYLIC ESTERS; NONDIAZO APPROACH; ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS;
D O I：
10.1002/anie.201805676
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C-H insertion and cyclopropanation of donor/donor carbenes are reported. The Ru-II/Pybox complex selectively catalyzed the intramolecular allylic C-H insertion, providing vinyl-substituted dihydroindoles with greater than 20:1 chemoselectivity and up to greater than 99% ee. Chiral dirhodium(II) tetracarboxylates, however, selectively promoted the intramolecular cyclopropanation, giving rise to cyclopropane-fused tetrahydroquinoline derivatives in excellent yields with greater than 99:1 chemoselectivity and up to 97% ee.
引用
收藏
页码：12405 / 12409
页数：5
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