Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by 1H NMR Spectroscopy

J Nat Prod. 2021 Jan 22;84(1):20-25. doi: 10.1021/acs.jnatprod.0c00828. Epub 2021 Jan 8.

Abstract

The structural elucidation of chiral molecules with more than one stereocenter is usually a tricky problem. In this paper, efficient 1H NMR spectroscopic approaches for assigning the erythro and threo configurations of 1-oxygenated 1,2-diarylpropan-3-ols were developed. By analysis of the chemical shift differences of diastereotopic methylene H2-3 (Δδ3) in CDCl3 or the chemical shift differences of H-1 and H-2 (Δδ1,2) in methanol-d4, deuterated dimethyl sulfoxide, and acetone-d6, the configurations of 1-oxygenated 1,2-diarylpropan-3-ols can be rapidly and conveniently determined.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Propanol / chemistry*
  • Dimethyl Sulfoxide / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Oxygen / chemistry*
  • Stereoisomerism

Substances

  • 1-Propanol
  • Oxygen
  • Dimethyl Sulfoxide