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

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

Authors :
Guan-Wu Wang
Ya-Wei Dong
Ping Wu
Ting-Ting Yuan
Ye-Bing Shen
Source :
Journal of Organic Chemistry. Sept 19, 2008, Vol. 73 Issue 18, 7088-7095
Publication Year :
2008

Abstract

Manganese(III) acetate dihydrate-mediated cycloadditions of 5,5-dimethyl-1,3-cyclohexanedione and 1,3-cyclohexanedione to various 1-(pyridine-2-yl)-enones to obtain trans-2-acyl-3-aryl/alkyl-2,3,6,7-tetrahydro-4(5H)-benzofuranone derivatives is reported. The cyclization reaction carried out under solvent-free ball-milling conditions exhibited good to excelled yields with extremely high diastereoselectivity and unexpected regioselectivity.

Details

Language :
English
ISSN :
00223263
Volume :
73
Issue :
18
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.188011780