Gold-catalyzed cycloisomerization of alk-4-yn-1-ones

被引：71

作者：

Belting, Volker ^{[1
]}

Krause, Norbert ^{[1
]}

机构：

[1] Dortmund Univ Technol, D-44227 Dortmund, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 06期

关键词：

HIGHLY SUBSTITUTED FURANS; EFFICIENT SYNTHESIS; ALKYNYL KETONES; TANDEM CYCLOISOMERIZATION; CYCLIZATION; 2-(1-ALKYNYL)-2-ALKEN-1-ONES; NUCLEOPHILES; HYDROARYLATION; HYDROAMINATION; DIHYDROFURANS;

D O I：

10.1039/b819704k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Depending on the substitution pattern and the solvent, the gold-catalyzed cyclization of alk-4-yn-1-ones 1 affords different oxygen heterocycles under mild reaction conditions. Alkynones with one substituent at C-3 undergo a 5-exo-dig cycloisomerization to substituted furans 2, whereas a 6-endo-dig cyclization to 4H-pyrans 3 is observed with substrates bearing two substituents at C-3. In alcoholic solvents, alkylidene/benzylidene-substituted tetrahydrofuranyl ethers 4 are formed in a tandem nucleophilic addition/cycloisomerization.

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页码：1221 / 1225

页数：5

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