钯（II）催化的对映选择性7-氮杂苯并降冰片二烯与炔基苯胺的去对称化偶联反应
Enantioselective Palladium(II)-Catalyzed Desymmetrizative Coupling of 7-Azabenzonorbornadienes with Alkynylanilines.
作者信息
Meng Junjie, He Hui, Liu Qianru, Xu Hanhong, Huang Huicai, Ni Shao-Fei, Li Zhaodong
机构信息
National Key Laboratory of Green Pesticide, College of Materials and Energy, South China Agricultural University, Guangzhou, 510641, Guangdong, China.
Department of Chemistry, Shantou University, Shantou, 515063, Guangdong, China.
出版信息
Angew Chem Int Ed Engl. 2024 Jan 2;63(1):e202315092. doi: 10.1002/anie.202315092. Epub 2023 Nov 28.
A Pd -catalyzed, domino enantioselective desymmetrizative coupling of 7-azabenzonorbornadienes with alkynylanilines is disclosed herein. This operationally simple transformation generates three covalent bonds and two contiguous stereocenters with excellent enantio- and diastereo-selectivity. The resulting functionalized indole-dihydronaphthalene-amine conjugates served as an appealing platform to streamline the diversity-oriented synthesis (DOS) of other valuable enantioenriched compounds. DFT calculations revealed that the two stabilizing non-covalent interactions contributed to the observed enantioselectivity.
本文公开了一种钯催化的7-氮杂苯并降冰片二烯与炔基苯胺的多米诺对映选择性去对称偶联反应。这种操作简单的转化反应能够生成三个共价键和两个相邻的立体中心，具有出色的对映选择性和非对映选择性。所得的功能化吲哚-二氢萘-胺共轭物为简化其他有价值的对映体富集化合物的多样性导向合成（DOS）提供了一个有吸引力的平台。密度泛函理论（DFT）计算表明，两种稳定的非共价相互作用有助于实现所观察到的对映选择性。
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