Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 2, Pages 385-391Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001021
Keywords
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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