Access to Hexahydrocarbazoles: The Thorpe-Ingold Effects of the Ligand on Enantioselectivity

被引：30

作者：

Chen, Hao ^{[1
]}

Wang, Lijia ^{[1
]}

Wang, Feng ^{[1
]}

Zhao, Liu-Peng ^{[1
]}

Wang, Pan ^{[1
]}

Tang, Yong ^{[1
,2
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 24期

关键词：

copper; cyclizations; enantioselectivity; heterocycles; ligand effects; BIS(OXAZOLINE) COPPER(II) COMPLEXES; DIELS-ALDER REACTIONS; ASYMMETRIC CATALYSIS; INDOLE ALKALOIDS; KOPSIA; AKUAMMILINE; (+/-)-ASPIDOPHYLLINE; VERSATILE; CONSTRUCTION; STRATEGY;

D O I：

10.1002/anie.201700042

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel cyclization reaction of methylenemalonate with indoles is reported, and it provides efficient access to a variety of hexahydrocarbazoles. The enantioselective version was realized by a finely tuned ligand/Cu-II catalyst. The optically active hexahydrocarbazoles contain three quaternary carbon centers and are obtained in up to 99% yield with greater than 99: 1 d.r. and up to greater than 99% ee. This reaction can be carried out on gram scale and stereoselective transformation of the product led to the core structure of a series of alkaloids from Kopsia plants.

引用

页码：6942 / 6945

页数：4

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