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

Direct α-oxytosylation of carbonyl compounds:: One-pot synthesis of heterocycles
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DOI:
10.1021/ol701774y
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发表时间:
2007-09-27
期刊:
影响因子:
5.2
通讯作者:
Tomkinson, Nicholas C. O.
Tomkinson, Nicholas C. O.
中科院分区:
化学1区
文献类型:
--
作者:
John, Oliver R. S.;Killeen, Niall M.;Tomkinson, Nicholas C. O.

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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.