手性四氢-β-咔啉的构建：吲哚基二氢吡啶的不对称 Pictet-Spengler 反应。
Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines.
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China.
出版信息
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7440-7443. doi: 10.1002/anie.201703178. Epub 2017 May 23.
A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet-Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee). With this method, a formal synthesis of tangutorine and a total synthesis of deplancheine were achieved in a highly efficient manner.
通过手性磷酸催化吲哚基二氢吡啶的Pictet-Spengler 反应，高效合成了对映体富集的四氢-β-咔啉。该反应在温和的反应条件下进行，以良好至优异的收率（高达 96%）和高对映选择性（高达 99%ee）得到所需的手性四氢-β-咔啉。利用该方法，以高效的方式实现了唐古特乌头碱的形式合成和去甲德普兰辛的全合成。
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