Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism.
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.
Yaguchi
Yoshihiro
Y
Corporate Research and Development Division, Takasago International Corporation, 4-11, 1-Chome, Nishi-yawata, Hiratsuka city, Kanagawa 254-0073, Japan.
Nakahashi
Atsufumi
A
Miura
Nobuaki
N
Sugimoto
Daisuke
D
Monde
Kenji
K
Emura
Makoto
M
D002942:Circular Dichroism; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; C039281:furan