Controllable Cycilization Reactions of 2-(2′,3′-Allenyl)acetylacetates Catalyzed by Gold and Palladium Affording Substituted Cyclopentene and 4,5-Dihydrofuran Derivatives with Distinct Selectivity

被引：40

作者：

Jiang, Xuefeng ^{[1
]}

Ma, Xiaojing ^{[2
]}

Zheng, Zilong ^{[1
]}

Ma, Shengming ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 28期

基金：

中国国家自然科学基金;

关键词：

allenes; chemoselectivity; gold; palladium; regioselectivity;

D O I：

10.1002/chem.200800793

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Efficient room-temperature syntheses of cyclopentenes and 4,5-dihydrofurans with different substitution patterns were performed starting from the same materials (i.e., 2-(2',3'-allenyl)acetyl acetates). Depending on the choice of metal catalyst, the Au-catalyzed reaction afforded C-attack-5-endo cyclization products 2, whereas the Pd-catalyzed one led to the formation of O-attack-5-exo cyclization products 3. The selectivity may be explained by the steric and electronic effects of the substrates and catalysts.

引用

页码：8572 / 8578

页数：7

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