4.7 Article

P(NMe2)3-Mediated Reductive (1+4) Annulation Reaction of Isatins with Nitroalkenes: An Access to Spirooxindolyl Isoxazoline N-Oxides and Their Corresponding Isoxazolines

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JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 20, 页码 10997-11007

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01962

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  1. National Natural Science Foundation of China [21472096, J1103306]

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The reductive (1 + 4) annulation reaction of isatins and substituted nitroalkenes mediated by a trivalent phosphorus reagent has been realized for the first time, providing easy access to spirooxindolyl isoxazoline N-Oxides in moderate to excellent yields with a flexible substrate scope. This reaction presumably proceeds through a Michael addition intramolecular substitution sequence via active in situ generated Kukhtin-Ramirez zwitterions from isatins and P(NMe2)(3). It is also demonstrated that the spirooxindolyl isoxazoline N-oxides can be readily converted into the corresponding isoxazolines in good yields.

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