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Application of 3-Methyl-2-vinylindoles in Catalytic Asymmetric Povarov Reaction: Diastereo- and Enantioselective Synthesis of Indole-Derived Tetrahydroquinolines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2015-12-21 00:00:00 , DOI: 10.1021/acs.joc.5b02476
Wei Dai 1 , Xiao-Li Jiang 1 , Ji-Yu Tao 1 , Feng Shi 1
Affiliation  

The first application of 3-methyl-2-vinylindoles in catalytic asymmetric Povarov reactions has been established via the three-component reactions of 3-methyl-2-vinylindoles, aldehydes, and anilines in the presence of chiral phosphoric acid, providing easy access to chiral indole-derived tetrahydroquinolines with three contiguous stereogenic centers at high yields (up to 99%) and with excellent diastereo- and enantioselectivities (all >95:5 dr, up to 96% ee). This mode of catalytic asymmetric three-component reaction offers a step-economic and atom-economic strategy for accessing enantioenriched indole-derived tetrahydroquinolines with structural diversity and complexity.

中文翻译:

3-甲基-2-乙烯基吲哚在催化不对称Povarov反应中的应用:吲哚衍生的四氢喹啉的非对映和对映选择性合成

在手性磷酸的存在下,通过3-甲基-2-乙烯基吲哚,醛和苯胺的三组分反应,建立了3-甲基-2-乙烯基吲哚在催化不对称Povarov反应中的首次应用,从而可以轻松地获得手性吲哚衍生的四氢喹啉,具有三个连续的立体中心,产率高(高达99%),并且具有出色的非对映和对映选择性(全部> 95:5 dr,ee高达96%)。这种模式的催化不对称三组分反应模式提供了一步经济和原子经济的策略,可用于获取结构多样性和复杂性的对映体富集的吲哚衍生的四氢喹啉。
更新日期:2015-12-21
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