Liu Ming-Shang, Du Hai-Wu, Cui Jian-Fang, Shu Wei
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, Guangdong, P.R. China.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, 300071, Tianjin, P.R. China.
Angew Chem Int Ed Engl. 2022 Oct 10;61(41):e202209929. doi: 10.1002/anie.202209929. Epub 2022 Sep 1.
Three-membered cyclic structures are widely existing in natural products and serve as enabling intermediates in organic synthesis. However, the efficient and straightforward access to such structures with diversity remains a formidable challenge. Herein, a general and practical protocol to aziridines and cyclopropanes synthesis using free XH (X=C or N) with alkenes by thianthrenation is presented. This metal-free protocol features the direct aziridination and cyclopropanation with unprotected XH . Free sulfonamides, amides, carbamates, amines, and methylene with acidic protons, are good precursors, providing an attractive alternative for straightforward synthesis of aziridines and cyclopropanes from easily available starting materials.
三元环状结构广泛存在于天然产物中，并作为有机合成中的关键中间体。然而，高效且直接地获得具有多样性的此类结构仍然是一项艰巨的挑战。在此，我们报道了一种通用且实用的方法，通过噻蒽化反应，使用游离的XH（X = C或N）与烯烃合成氮杂环丙烷和环丙烷。这种无金属方法的特点是用未受保护的XH进行直接氮杂环丙烷化和环丙烷化反应。游离的磺酰胺、酰胺、氨基甲酸酯、胺以及带有酸性质子的亚甲基都是良好的前体，为从容易获得的起始原料直接合成氮杂环丙烷和环丙烷提供了一种有吸引力的替代方法。
