Direct Organocatalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imides to α-Ketoesters under Low Ligand Loading: A Doubly Stereocontrolled Approach to Cyclic Thiocarbamates Bearing Chiral Quaternary Stereocenters
Direct Organocatalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imides to α-Ketoesters under Low Ligand Loading: A Doubly Stereocontrolled Approach to Cyclic Thiocarbamates Bearing Chiral Quaternary Stereocenters
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DOI：
10.1021/ol1002829
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发表时间：
2010-04-02
期刊：
影响因子：
5.2
通讯作者：
Wang, Rui
中科院分区：
文献类型：
--
作者：
Jiang, Xianxing;Zhang, Gen;Wang, Rui
本文首次采用松香衍生叔胺硫脲在低配体负荷下对-异硫氰酸亚胺与-酮酯进行双立体控制有机催化不对称醛醇反应，生成了具有高水平对映和非对映选择性（高达99% ee， 97:3 dr）的含季立体中心的环硫氨基甲酸酯。该反应为获得高光学纯度的合成有用的多取代环硫代氨基甲酸酯提供了方便的双立体控制方法。
The first doubly stereocontrolled organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides with alpha-ketoesters by using rosin-derived tertiary amine-thiourea under low ligand loading to form cyclic thiocarbamates bearing quaternary stereogenic centers with high levels of enantio- and diastereoselectivity (up to 99% ee, and 97:3 dr) is presented. This reaction provides a convenient doubly stereocontrolled method to access synthetic useful multiply substituted cyclic thiocarbamates with high optical purity.