Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 18, Pages 7088-7095Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo800870z
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Funding
- National Natural Science Foundation of China [20621061, 20772117]
- National Basic Research Program of China [2006CB922003]
- Scientific Research Foundation of Graduate School of USTC
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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.
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