Journal
ORGANIC LETTERS
Volume 9, Issue 20, Pages 4009-4012Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol701774y
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- Engineering and Physical Sciences Research Council [GR/T04113/01] Funding Source: researchfish
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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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