Qian Guangyin, Bai Miao, Gao Shijun, Chen Han, Zhou Siwei, Cheng Hong-Gang, Yan Wei, Zhou Qianghui
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
The Institute for Advanced Studies, Wuhan University, Wuhan, 430072, China.
Angew Chem Int Ed Engl. 2018 Aug 20;57(34):10980-10984. doi: 10.1002/anie.201806780. Epub 2018 Jul 23.
Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.
报道了一种使用卡泰拉尼策略的模块化一步三组分合成四氢异喹啉的方法。该过程利用氮丙啶作为烷基化试剂，通过钯/降冰片烯协同催化，实现卡泰拉尼/赫克/氮杂迈克尔加成串联反应。这种温和、化学选择性且可扩展的方法具有广泛的底物范围（43个例子，产率高达90%）。该方法最显著的特点是，对于2-烷基和2-芳基取代的氮丙啶，分别得到1,3-顺式取代和1,4-顺式取代的四氢异喹啉时，观察到了优异的区域选择性和非对映选择性。此外，这是一个具有高步骤经济性和原子经济性的通用过程。
