title: Preparation of Optically Active δ-Tri- and δ-Tetradecalactones by a Combination of Novozym 435-catalyzed Enantioselective Methanolysis and Amidation.
abstract: A combination of Novozym 435-catalyzed methanolysis and amidation using racemic N-methyl-5-acetoxytridecan- and tetradecanamides as a substrate proceeded in good enantioselectivity to afford the corresponding (R)-N-methyl-5-acetoxyalkanamides, (S)-N-methyl-5-hydroxyalkanamides, and (S)-N-cyclohexyl-5-hydroxyalkanamides. Both enantiomers of δ-tri- and δ-tetradecalactones were synthesized in over 90% enantiomeric excesses from the corresponding (R)- or (S)-alkanamides. Addition of cyclohexylamine to Novozym 435-catalyzed methanolysis shortened 24-hour reaction time to reach about 50% conversion. Enantiomers of optically active δ-tri- and δ-tetradecalactones had different odors and thresholds.
authors.affiliation: Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology.
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Shimotori
authors.forename: Masayuki
authors.initials: M
authors.lastname: Hoshi
authors.forename: Hayato
authors.initials: H
authors.lastname: Okabe
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Miyakoshi
mesh_terms: D002384:Catalysis; D003514:Cyclohexylamines / Q000737:chemistry; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007783:Lactones / Q000138:chemical synthesis*; D008049:Lipase / Q000737:chemistry*; D009812:Odorants; D055601:Organic Chemistry Phenomena; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: D003514:Cyclohexylamines; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007783:Lactones; D011753:Pyrones; C093667:Novozyme 435; D008049:Lipase