期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 40, 页码 12207-12213出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201001461
关键词
alkynes; cyclization; gold; heterocycles; iron
资金
- CNRS
- Institut de Chimie des Substances Naturelles
- MESR
The use N-sulfonyl-protected hydroxylamines as bi-nucleophiles in iron-catalyzed propargylic substitutions allows the selective one-pot synthesis of four classes of substituted isoxazoles or isoxazolines from the same propargylic alcohols (21 examples) by simply tuning the nature of the base. By using an iron(III) catalyst and a base such as triethylamine (3 equiv), isoxazoles 3 are obtained in good isolated yields (56-95%), whereas N-sulfonyl-protected isoxazolines 6 are selectively obtained (77-93% yield) by using iron and gold catalysts in the presence of a catalytic amount of pyridine (10 mol%).
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