Ruthenium-catalyzed one-pot double allylation/cycloisomerization of 1,3-dicarbonyl compounds leading to exo-methylenecyclopentanes

被引：40

作者：

Yamamoto, Y ^{[1
]}

Nakagai, Y ^{[1
]}

Itoh, K ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Nagoya, Aichi 4648603, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 01期

关键词：

alkenes; allylation; cycloisomerization; homogeneous; catalysis; ruthenium;

D O I：

10.1002/chem.200305340

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ruthenium-catalyzed one-pot double allylation/cycloisomerization of 1,3-diketones and methyl acetoacetate gave exo-methylenecyclopentanes in moderate to good yields with high isomer selectivity. The double allylation step effectively proceeded in the presence of a Ru-II precatalyst, [Cp*RuCl(cod)], in 1,2-dichloroethane at 90degreesC. The subsequent cycloisomerization was carried out upon addition of triethylsilane as a hydride source without purification of a 1,6-diene intermediate. Detailed inspections of the reaction by H-1 NMR spectroscopy disclosed that triethylsilyl methyl ether plays an important role for the conversion of a ruthenium(IV) allyl complex formed in the double allylation step into a ruthenium(II) species required for the cycloisomerization.

引用

页码：231 / 236

页数：6

共 58 条

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