Oxime radical promoted dioxygenation, oxyamination, and diamination of alkenes: synthesis of isoxazolines and cyclic nitrones |
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| Authors: | Bing Han Xiu-Long Yang Ran Fang Wei Yu Chao Wang Xiao-Yong Duan Shuai Liu |
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| Affiliation: | State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China). hanb@lzu.edu.cn. |
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| Abstract: | Up the tempo: The intramolecular addition of oxime radicals to C?C bonds was achieved by using DEAD and TEMPO to give 4,5-dihydroisoxazoles as a result of a C?O bond-forming, 5-exo-trig cyclization. γ,δ-Unsaturated ketoximes also reacted to afford cyclic nitrones through C?N bond formation. The reactions offer a metal-free approach for the vicinal difunctionalization of unactivated alkenes. |
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| Keywords: | alkenes cyclization heterocycles radicals synthetic methods |
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