4.5 Article

Synthesis of Aziridine- and Oxirane-2-phosphonates Spiro-Fused with Oxindoles

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 2, 页码 385-391

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001021

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Epoxidation; Heterocycles; Indoles; Small ring systems; Spiro compounds; Wittig reactions

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3-(Phosphorylmethylene)oxindoles have been prepared by a straightforward Horner-Wadsworth-Emmons reaction. They were treated with ethyl N-{[(4-nitrophenyl)sulfonyl]oxy}-carbamate (NsONHCO(2)Et) in the presence of CaO to afford new aziridine-2-phosphonates spiro-fused with oxindole. 3(Phosphorylmethylene)oxindoles were also transformed into novel spiro[oxindole-oxiranes] by reaction with H2O2/NaOH.

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