具有中心手性转位的催化不对称烯丙基取代/异构化反应
Catalytic Asymmetric Allylic Substitution/Isomerization with Central Chirality Transposition.
作者信息
Han Zhengyu, Zhuang Han, Tang Luning, Zang Yu, Guo Wengang, Huang Hai, Sun Jianwei
机构信息
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
Department of Chemistry and Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.
出版信息
Org Lett. 2022 Jun 17;24(23):4246-4251. doi: 10.1021/acs.orglett.2c01559. Epub 2022 Jun 3.
We have developed a catalytic asymmetric allylic substitution/isomerization process with central chirality transposition. This process takes advantage of the ambident reactivity of the 2-indole imine methide generated from racemic tertiary indolylmethanols. The use of a suitable chiral phosphoric acid catalyst and an -directing group allowed regioselective formation a C-C bond at the 3 position but enantiocontrolled construction of a stereogenic center at the 2-benzylic position.
我们开发了一种具有中心手性转位的催化不对称烯丙基取代/异构化过程。该过程利用了由外消旋叔吲哚基甲醇生成的2-吲哚基亚胺甲基化物的双亲核反应性。使用合适的手性磷酸催化剂和一个导向基团可实现3位区域选择性地形成C-C键，同时在2-苄基位置对映体控制地构建一个立体中心。
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