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January 1, 1977The Journal of Organic Chemistry

Nuclear magnetic resonance determination of enantiomeric composition and absolute configuration of .gamma.-lactones using chiral 2,2,2-trifluoro-1-(9-anthryl)ethanol

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Authors

WPWilliam H. PirkleUniversity of Illinois Urbana-ChampaignDSDavid L. SikkengaUniversity of Illinois Urbana-ChampaignMPMark S. PavlinSavannah State University

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Overview

Spectroscopic analysis demonstrates chiral resolution of gamma-lactones using fluorinated anthrylethanol, indicating a reliable NMR route for stereochemical assignment.

Key Points

  • Establish a nuclear magnetic resonance (NMR) spectroscopic approach to assign the enantiomeric purity and absolute configuration of gamma-lactones.
  • Employed chiral 2,2,2-trifluoro-1-(9-anthryl)ethanol as a chiral solvating agent in NMR spectroscopy.
  • Analyzed diastereomeric interactions and chemical shift nonequivalence across gamma-lactone enantiomers.
  • Chiral solvating agent produces distinct NMR signal splitting between enantiomeric pairs of gamma-lactones.
  • Observed chemical shift differences directly correlate with absolute stereochemical configuration without requiring covalent derivatization.

Cite This Study

Pirkle et al. (1977) studied this question.

synapsesocial.com/papers/6a9377032aef8ffffdabdd8ahttps://doi.org/10.1021/jo00422a061
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