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Direct alpha-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles. 2007

Oliver R S John, and Niall M Killeen, and Deborah A Knowles, and Sze Chak Yau, and Mark C Bagley, and Nicholas C O Tomkinson
School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, United Kingdom.

N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct alpha-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.

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