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

The Journal of Organic Chemistry
Guan-Wu WangYe-Bing Shen

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.

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Citations

Apr 8, 2009·Molecular Diversity·Xiang-Qiang PanWei Zhang
Nov 17, 2015·The Journal of Organic Chemistry·Kenneth N BoblakDouglas A Klumpp
May 11, 2013·Chemical Society Reviews·Guan-Wu Wang
Mar 10, 2011·Chemical Society Reviews·Achim StolleBernd Ondruschka
Nov 2, 2011·Organic & Biomolecular Chemistry·Sandro CacchiGuillaume Prestat
Feb 19, 2009·Journal of the American Chemical Society·Burçak IçliKay Severin
Sep 11, 2009·The Journal of Organic Chemistry·Qi-Fang WangChao-Guo Yan
Apr 24, 2009·The Journal of Organic Chemistry·Zhiqi CongHiroshi Nishino

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