通过硫醇引发的非对映和对映选择性双迈克尔加成反应实现3-硝基吲哚和3-硝基苯并噻吩的有机催化不对称去芳构化反应
Organocatalytic Asymmetric Dearomatization of 3-Nitroindoles and 3-Nitrobenzothiophenes via Thiol-Triggered Diastereo- and Enantioselective Double Michael Addition Reaction.
作者信息
Chen Xin-Meng, Lei Chuan-Wen, Yue Deng-Feng, Zhao Jian-Qiang, Wang Zhen-Hua, Zhang Xiao-Mei, Xu Xiao-Ying, Yuan Wei-Cheng
机构信息
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry , Chinese Academy of Sciences , Chengdu 610041 , China.
University of Chinese Academy of Sciences , Beijing 100049 , China.
出版信息
Org Lett. 2019 Jul 19;21(14):5452-5456. doi: 10.1021/acs.orglett.9b01688. Epub 2019 Jun 28.
Organocatalytic asymmetric dearomatization of 3-nitroindoles and 3-nitrobenzothiophenes by reaction with ethyl 4-mercapto-2-butenoate has been developed. A range of chiral tetrahydrothiopheneindolines and tetrahydrothiophenebenzothiophenes bearing three contiguous stereocenters are obtained in high yields with good diastereoselectivities and excellent enantioselectivities. This is the first example of thiol-triggered catalytic asymmetric dearomatization of 3-nitroindoles and 3-nitrobenzothiophenes.
已开发出通过与4-巯基-2-丁烯酸乙酯反应实现3-硝基吲哚和3-硝基苯并噻吩的有机催化不对称去芳构化反应。一系列带有三个相邻立体中心的手性四氢噻吩并吲哚啉和四氢噻吩并苯并噻吩以高收率、良好的非对映选择性和优异的对映选择性得到。这是3-硝基吲哚和3-硝基苯并噻吩的硫醇引发的催化不对称去芳构化的首个实例。
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