title: Unexpected solvent-free cycloadditions of 1,3-cyclohexanediones to 1-(pyridin-2-yl)-enones mediated by manganese(III) acetate in a ball mill.
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.
authors: Hefei National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China. gwang@ustc.edu.cn
authors: Guan-Wu
authors: GW
authors: Wang
authors: Ya-Wei
authors: YW
authors: Dong
authors: Ping
authors: P
authors: Wu
authors: Ting-Ting
authors: TT
authors: Yuan
authors: Ye-Bing
authors: YB
authors: Shen
mesh_terms: D000085:Acetates / Q000737:chemistry*; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
chemical_list: C532719:1-(pyridin-2-yl)-enone; D000085:Acetates; D003512:Cyclohexanones; D009942:Organometallic Compounds; D016877:Oxidants; D011728:Pyridones; D012997:Solvents; C521134:manganese(III) acetate dihydrate; C004636:1,3-cyclohexanedione