Palladium-catalyzed intramolecular oxidative alkylation of 4-pentenyl β-dicarbonyl compounds

被引：24

作者：

Liu, C ^{[1
]}

Wang, X ^{[1
]}

Pei, T ^{[1
]}

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 24期

关键词：

C-C coupling; cyclization; enols; homogeneous; catalysis; palladium;

D O I：

10.1002/chem.200400460

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of 8-nonene-2,4-dione with a catalytic amount of [PdCl2(CH3CN)(2)] (2; 5 mol %) and a stoichiometric amount of CuCl2 (2.5 equiv) at room temperature for 3 h led to oxidative alkylation and formation of 2-acetyl-3-methyl-2-cyclohexenone in 80% isolated yield. The oxidative alkylation of 4-pentenyl beta-diketones tolerated a number of terminal acyl groups and substitution at the C1 and C3 carbon atoms of the 4-pentenyl chain. Likewise, 4-pentenyl P-keto esters that possessed germinal disubstitution at the C1, C2, or C3 carbon atom of the 4-pentenyl chain cyclized to form 2-carboalkoxy-2-cyclohexenones in moderate to good yield as the exclusive cyclized product. Deuterium-labeling experiments provided information regarding the mechanism of the palladium-catalyzed oxidative alkylation of 4-pentenyl P-dicarbonyl compounds.

引用

页码：6343 / 6352

页数：10

共 48 条

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