Organic Letters p. 4009 - 4012 (2007)
Update date:2022-07-30
Topics:
John, Oliver R. S.
Killeen, Niall M.
Knowles, Deborah A.
Yau, Sze Chak
Bagley, Mark C.
Tomkinson, Nicholas C. O.
N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct α-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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