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

页码：12405 / 12409

页数：5