Catalytic asymmetric dearomative azo-Diels-Alder reaction of 2-vinlyindoles

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外文摘要：Due to the high electrophilic nature of azo-dienophiles,azo-Diels-Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the"click reaction".This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version.Reported herein is the first catalytic asymmetric dearomative azo-Diels-Alder reaction between 2-vinylindoles and triazoledione.This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels-Alder reaction,allowing the implementation of the projected reaction at ambient temperature.Density functional theory calculations have been performed to gain insights into the reaction mechanism and the origins of the enantioselectivity.By using this method,a variety of tetracyclic indole derivatives have been readily prepared in good to excellent yields and with excellent diastereo-and enantio-selectivities(33 examples,up to 97％yield and＞99％ee,＞20:1 dr).

外文关键词：

Catalytic asymmetric dearomatizationAzo-Diels-Alder reaction2-VinylindolesChiral phosphoric acidTetracyclic indole derivatives

作者：

Yu-Hang Miao、Zheng-Xu Zhang、Xu-Yi Huang、Yuan-Zhao Hua、Shi-Kun Jia、Xiao Xiao、Min-Can Wang、Li-Ping Xu、Guang-Jian Mei

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作者单位：

Green Catalysis Center,and College of Chemistry,Zhengzhou University,Zhengzhou 450052,China

School of Chemistry and Chemical Engineering,Shandong University of Technology,Zibo 255000,China

Institute of Pharmaceutical Science and Technology,Zhejiang University of Technology,Hangzhou 310014,China

基金：

河南省自然科学基金appli-cation research plan of Key Scientific Research Projects in Colleges and Universities of Henan ProvinceYouth In-novation Team Program in Colleges and Universities of Shandong Province国家自然科学基金

项目编号：

22230042008422A1500562022KJ22822208302

出版年：

2024

DOI：

10.1016/j.cclet.2023.108830

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(4)

参考文献量65