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

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 <i>erythro</i> and <i>threo</i> 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 (Δδ_1,2) in methanol-<i>d</i>₄, deuterated dimethyl sulfoxide, and acetone-<i>d</i>₆, the configurations of 1-oxygenated 1,2-diarylpropan-3-ols can be rapidly and conveniently determined.