Stereochemical Study of Chiral Tautomeric Flavorous Furanones by Vibrational Circular Dichroism

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 clarifi...

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Veröffentlicht in:Organic letters 2008-11, Vol.10 (21), p.4883-4885
Hauptverfasser: Yaguchi, Yoshihiro, Nakahashi, Atsufumi, Miura, Nobuaki, Sugimoto, Daisuke, Monde, Kenji, Emura, Makoto
Format: Artikel
Sprache:eng
Schlagworte:
Circular Dichroism
Furans - chemistry
Models, Molecular
Molecular Structure
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801966t