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.

Sulfones P 0450Direct α-Oxytosylation of Carbonyl Compounds: One-Pot Synthesis of Heterocycles. -Reagent (II) is found to be general to give α-tosylation products of cyclic and linear ketones with high regioselectivity. A one-pot method is developed for the direct formation of heterocyclic products from carbonyl compounds by addition of a bis-nucleophile to the reaction mixture and heating to promote a cyclo-condensation process. -(JOHN, O. R. S.; KILLEEN, N. M.; KNOWLES, D. A.; YAU, S. C.; BAGLEY, M. C.; TOMKINSON*, N. C. O.; Org. Lett. 9 (2007) 20, 4009-4012; Sch. Chem., Cardiff Univ., Cardiff CF10 3AT, UK; Eng.) -R. Steudel 12-063