手性螺环芳烃的铑催化 C-H 环化反应的对映选择性合成。
Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C-H Annulation with Alkynes.
机构信息
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Chang-Kung Chuang Institute, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.
出版信息
J Am Chem Soc. 2021 Jan 13;143(1):114-120. doi: 10.1021/jacs.0c11735. Epub 2020 Dec 24.
A rhodium(III)-catalyzed enantioselective C-H activation/annulation process is disclosed. With a catalyst derived from a chiral CpRh(III) complex and a chiral acid, the direct annulation reactions between 1-aryl isoquinoline derivatives and alkynes take place smoothly to afford a series of chiral azoniahelicenes in excellent yields and enantioselectivity (up to 99% yield and 96% ee). Mechanistic studies suggest that C-H bond cleavage may be the turnover-limiting step.
一种铑(III)催化的对映选择性 C-H 活化/环化反应被揭示。使用手性 CpRh(III)配合物和手性酸衍生的催化剂，1-芳基异喹啉衍生物和炔烃之间的直接环化反应顺利进行，以高收率和对映选择性（高达 99%的收率和 96%的对映体过量）得到一系列手性氮杂薁。机理研究表明，C-H 键的断裂可能是决定反应速率的步骤。
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