[reaction: see text] Electroreduction of styrenes or alkyl methacrylates in the presence of aliphatic acid anhydrides or N-acylimidazoles with an undivided cell equipped with zinc electrodes as the anode and the cathode brought about novel one-pot vicinal double C-acylation to afford the corresponding 1,4-diketones in satisfactory yields.

Background: JMJD1A specifically demethylates mono-and dimethyl-histone H3K9. Results: Two active sites of JMJD1A homodimer cooperatively demethylate dimethylated H3K9. Conclusion: Homodimerization of JMJD1A is essential for appropriate control of histone methylation state. Significance: The novel demethylation mechanism of JMJD1A will help in understanding the histone code.

Anodic oxidation of 1-acetoxy-3,4-dihydronaphthalene (1) and alpha-acetoxy-beta-alkylstyrenes (3) at -78 degrees C in a mixed solvent of acetonitrile (CH(3)CN), tetrahydrofuran (THF), and acetic acid (AcOH) containing (S)-tetraethylammonium camphorsulfonate as a chiral supporting electrolyte brought about enantioselective formation of the corresponding 2-acetoxy-1-tetralones (2) and (R)-2-acetoxy-1-phenyl-1-alkanone (4) with maximum enantiomeric excess (ee) of 44% and 21%, respectively. Introduction of a 7-methoxy group into 1 and increase in bulkiness of a beta-alkyl group in 3 resulted in improvement of enantioselectivity of the reactions.

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This study showed some decrease in stereoselectivity in electroreductive intramolecular cyclization of nitrogen-containing non-conjugated enones in comparison with high stereoselectivity for the corresponding enones possessing an all-carbon-chain or a sulfur-containing chain. This phenomenon may provide some actual experimental supports for the remarkable stereochemical features of the electroreductive cyclization.

Electrolysis Electrolysis M 4000Novel One-Pot Vicinal Double C-Acylation of Styrenes and Methacrylates by Electroreduction. -1,4-Diketones are synthesized in satisfactory yields by electroreduction of styrenes or alkyl methacrylates in the presence of aliphatic acid anhydrides or N-acylimidazoles in an undivided cell equipped with zinc electrodes as the anode and the cathode. In some cases, only monoacylation products are obtained. -(YAMAMOTO, Y.; MAEKAWA, H.; GODA, S.; NISHIGUCHI*, I.; Org. Lett. 5 (2003) 15, 2755-2758; Dep. Chem., Nagaoka Univ. Technol., Nagaoka, Niigata 940-21, Japan; Eng.) -Klein 47-024

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