Unexpected solvent-free cycloadditions of 1,3-cyclohexanediones to 1-(pyridin-2-yl)-enones mediated by manganese(III) acetate in a ball mill.
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.
Wang
Guan-Wu
GW
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
Dong
Ya-Wei
YW
Wu
Ping
P
Yuan
Ting-Ting
TT
Shen
Ye-Bing
YB
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
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