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

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)


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
Issue number20
Publication statusPublished - 2007


  • carbonyl compounds
  • one-pot synthesis
  • heterocycles

Fingerprint Dive into the research topics of 'Direct α-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles'. Together they form a unique fingerprint.

Cite this