Yan Xu, Wang Fang, Peng Tonghui, He Yulong, Zhang Qing-Bao, Yang Yang
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, People's Republic of China.
Department of Pharmacy, Renmin Hospital of Wuhan University, Wuhan 430060, People's Republic of China.
J Org Chem. 2025 Jan 10;90(1):806-813. doi: 10.1021/acs.joc.4c02801. Epub 2024 Dec 31.
A novel copper-catalyzed formal diastereoselective [4 + 3] cycloaddition of 2-arylaziridines and 2-substituted cyclopentadiene was developed. This transformation provided an efficient protocol for the assembly of a highly strained bridged azabicyclo[3.2.1]octane scaffold, which is widespread in bioactive natural products. A likely mechanism showed that the reaction proceeds through [3 + 2] cycloaddition, ring opening, and aza-Michael addition cascade reaction. This protocol features high efficiency and diastereoselectivity, wide functional group compatibility, and a cheap catalyst.
开发了一种新型铜催化的2-芳基氮杂环丙烷与2-取代环戊二烯的形式非对映选择性[4 + 3]环加成反应。这种转化为构建高度张力的桥连氮杂双环[3.2.1]辛烷骨架提供了一种有效的方法，该骨架广泛存在于生物活性天然产物中。一种可能的机理表明，该反应通过[3 + 2]环加成、开环和氮杂迈克尔加成串联反应进行。该方法具有高效、非对映选择性高、官能团兼容性广和催化剂廉价等特点。
