Highly Diastereo- and Enantioselective Synthesis of Quinuclidine Derivatives by an Iridium-Catalyzed Intramolecular Allylic Dearomatization Reaction

被引：38

作者：

Huang, Lin ^{[1
]}

Cai, Yue ^{[1
]}

Zhang, Hui-Jun ^{[1
]}

Zheng, Chao ^{[1
]}

Dai, Li-Xin ^{[1
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, State Key Lab Organometall Chem, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

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

来源：

CCS CHEMISTRY | 2019年 / 1卷 / 01期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; dearomatization; indole; iridium;

D O I：

10.31635/ccschem.019.20180006

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl](2) and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%-96%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee). These products feature versatile functional group diversity and can undergo diverse transformations. A model that accounts for the origin of the stereoselectivity has been proposed based on density functional theory (DFT) calculations.

引用

页码：106 / 116

页数：11

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