Unexpected solvent-free cycloadditions of 1,3-cyclohexanediones to 1-(pyridin-2-yl)-enones mediated by manganese(III) acetate in a ball mill

被引：87

作者：

Wang, Guan-Wu ^{[1
]}

Dong, Ya-Wei

Wu, Ping

Yuan, Ting-Ting

Shen, Ye-Bing

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Joint Lab Green Synthet Chem, Hefei 230026, Anhui, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 18期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/jo800870z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under solvent-free ball-milling conditions, manganese(III) acetate dihydrate-mediated cycloadditions of 5,5-dimethyl-1,3-cyclohexanedione and 1,3-cyclohexanedione to various 1-(pyridin-2-yl)-enones proceeded efficiently to afford trans-2-acyl-3-aryl/alkyl-2,3.6,7-tetrahydro-4(5H)-benzofuranone derivatives. The cyclization reactions exhibited good to excellent yields, as well as extremely high diastereoselectivity and unexpected regioselectivity. Manganese(III) acetate behaved both as an oxidant and as a Lewis acid.

引用

页码：7088 / 7095

页数：8

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