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

The structural elucidation of chiral molecules with more than one stereocenter is usually a tricky problem. In this paper, efficient H-1 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 H-2-3 (Delta delta(3)) in CDCl3 or the chemical shift differences of H-1 and H-2 (Delta delta(1,2)) in methanol-d(4), deuterated dimethyl sulfoxide, and acetone-d(6) , the configurations of 1-oxygenated 1,2-diarylpropan-3-ols can be rapidly and conveniently determined.

Automated summary

Efficient H-1 NMR spectroscopic approaches were developed for assigning the erythro and threo configurations of 1-oxygenated 1,2-diarylpropan-3-ols. The configurations can be rapidly and conveniently determined through chemical shift analysis in different solvents.