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

John, Oliver R. S. and Killeen, Niall M. and Knowles, Deborah A. and Yau, Sze Chak and Bagley, Mark C. and Tomkinson, Nicholas C. O. (2007) Direct α-oxytosylation of carbonyl compounds : one-pot synthesis of heterocycles. Organic Letters, 9 (20). pp. 4009-4012. ISSN 1523-7060

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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)]