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Efficient regioselective aldol condensation of methyl ketones promoted by organoaluminum compounds,and its application to muscone synthesis
Authors:Jiro Tsuji  Toshiro Yamada  Mitsumasa Kaito  Tdakatsu Mandai
Institution:Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
Abstract:Regioselective aldol condensation of 2-octanone and 2-butanone at the methyl side proceeded in high yields using a system of dialkylaluminum phenoxide/tertiary amine. The intramolecular aldol condensation of 2,15-hexadecanedione was carried out by the same system, especially di-i-butylaluminum phenoxide/pyridine, to give dehydromuscone in 65% yield. Its hydrogenation afforded muscone (3-methylcyclopentadecanone).
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