A Versatile Iron-Catalyzed Protocol for the One-Pot Synthesis of Isoxazoles or Isoxazolines from the Same Propargylic Alcohols

被引：62

作者：

Debleds, Olivier ^{[1
]}

Gayon, Eric ^{[1
]}

Ostaszuk, Emilie ^{[1
]}

Vrancken, Emmanuel ^{[1
]}

Campagne, Jean-Marc ^{[1
]}

机构：

[1] CNRS UM2 UM1ENSCM, UMR 5253, Inst Charles Gerhardt, F-34296 Montpellier 5, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 40期

关键词：

alkynes; cyclization; gold; heterocycles; iron; HIGHLY SUBSTITUTED ISOXAZOLES; COPPER(I)-CATALYZED SYNTHESIS; 3,5-DISUBSTITUTED ISOXAZOLES; NUCLEOPHILIC-SUBSTITUTION; ELECTROPHILIC CYCLIZATION; NITRILE OXIDES; EFFICIENT; CYCLOADDITION; OXIMES; CYCLOISOMERIZATION;

D O I：

10.1002/chem.201001461

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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%).

引用

页码：12207 / 12213

页数：7

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