title: Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism.
abstract: 2-Substituted-3(2H)-furanone derivatives are industrially significant aroma compounds possessing a unique keto-enol tautomeric feature causing their racemization. Absolute configurations of two flavorous furanones, which have remained unclear for the past 40 years since their discovery, were clarified by the vibrational circular dichroism technique as well as chemical relay reactions. Odor evaluation of each enantiomer revealed relationships between their configurations and their odor activities.
authors.affiliation: Corporate Research and Development Division, Takasago International Corporation, 4-11, 1-Chome, Nishi-yawata, Hiratsuka city, Kanagawa 254-0073, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Yaguchi
authors.forename: Atsufumi
authors.initials: A
authors.lastname: Nakahashi
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Miura
authors.forename: Daisuke
authors.initials: D
authors.lastname: Sugimoto
authors.forename: Kenji
authors.initials: K
authors.lastname: Monde
authors.forename: Makoto
authors.initials: M
authors.lastname: Emura
mesh_terms: D002942:Circular Dichroism; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; C039281:furan