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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

Guan-Wu Wang, Ya-Wei Dong, Ping Wu, Ting-Ting Yuan, Ye-Bing Shen

J Org Chem. 2008 Sep 19;73(18):7088-95.

PMID: 18710288

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP19513054 Manganese(III) acetate dihydrate Manganese(III) acetate dihydrate 19513-05-4 Price
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