Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences , Soochow University , 199 Ren-Ai Road , Suzhou , Jiangsu 215123 , People's Republic of China.
Org Lett. 2020 Feb 7;22(3):1222-1226. doi: 10.1021/acs.orglett.0c00224. Epub 2020 Jan 27.
Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates -selective coupling products with excellent chemo- and stereoselectivity.
含氮杂环广泛存在于天然和合成的生物活性分子中。我们在此报告了一种前所未有的通过光氧化还原和钴卟啉协同催化α-亚氨基-氧代酸与烯丙基化合物进行自由基氮杂环化的方法。无论是否有烯烃作为分子间交叉偶联伙伴,该转化都能以令人满意的收率提供各种相应的含烯烃的二氢吡咯产物。在外烯存在下,串联反应以优异的化学和立体选择性生成 -选择性偶联产物。