Direct α-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles

Oliver R. S. John, Niall M. Killeen, Deborah A. Knowles, Sze Chak Yau, Mark C. Bagley, Nicholas C. O. Tomkinson

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34 Citations (Scopus)

Abstract

N-Methyl-O-tosylhydroxylamine (I) is an effective reagent for the direct α-oxytosylation of carbonyl compds. The reactions proceed smoothly at room temp. in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsym. substrates, regioselectivity for primary over secondary centers is obsd. and complete regiospecificity for primary over tertiary centers is obtained. E.g., reaction of I and PhCOCH2CH3 gave 48% PhCOCHMeOTs. Addn. of a bis-heteronucleophile directly to the crude reaction mixt. in a one-pot process leads to the corresponding heterocyclic product. E.g., reaction of I and acetone, followed by addn. of H2NCSPh, gave 69% 4-methyl-2-phenylthiazole. [on SciFinder(R)]
Original languageEnglish
Pages (from-to)4009-4012
Number of pages4
JournalOrganic Letters
Volume9
Issue number20
DOIs
Publication statusPublished - 2007

Keywords

  • carbonyl compounds
  • one-pot synthesis
  • heterocycles

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    John, O. R. S., Killeen, N. M., Knowles, D. A., Yau, S. C., Bagley, M. C., & Tomkinson, N. C. O. (2007). Direct α-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles. Organic Letters, 9(20), 4009-4012. https://doi.org/10.1021/ol701774y