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Application of αMNPA to stereochemical studies of monoterpene alcohol
Author(s) -
Ichikawa Akio
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:1<70::aid-chir12>3.0.co;2-p
Subject(s) - chemistry , monoterpene , propanoic acid , citronellol , enantiomer , menthol , chirality (physics) , alcohol , diastereomer , stereochemistry , nuclear magnetic resonance spectroscopy , reagent , organic chemistry , geraniol , chromatography , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , essential oil , quark
2‐Methoxy‐2‐(1‐naphthyl)propanoic acid (αMNPA) was used to study monoterpene alcohol stereochemically. This reagent has both a rigid chiral center and a high‐resolution naphthyl group for 1 H‐NMR and HPLC analysis. Enantiomeric resolution of citronellol was considered using (−)‐αMNPA and the Mosher‐Trost method was applied to (−)‐menthol using (−)‐ and (+)‐αMNPA. An S configuration is proposed for (−)‐αMNPA based on 1 H‐NMR spectroscopy data. Chirality 11:70–74, 1999. © 1999 Wiley‐Liss, Inc.