Efficient Regioselective Aldol Condensation of Methyl Ketones Promoted by Organoaluminium Compounds, and Its Application to Muscone Synthesis

Abstract

Abstract Dialkylaluminium aryloxide in combination with a tertiary amine was found to be a good reagent for regioselective aldol condensation of methyl ketones at the methyl side. Regioselective aldol condensation of 2-octanone was carried out using diisobutylaluminium phenoxide–pyridine. The intramolecular aldol condensation of 2,15-hexadecanedione promoted by the same reagent gave a mixture of dehydromuscones in 65% yield. Its hydrogenation produced muscone.