Rapid Approaches for Assignment of the Relative Configuration in 1-Oxygenated 1,2-Diarylpropan-3-ols by <sup>1</sup>H NMR Spectroscopy
Le Zhou, Rui Guo, Han Zhang, Liwei Lu, Ye‐Qing Du, Qingbo Liu, Xiao‐Xiao Huang, Shao‐Jiang Song
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.
Topics & Concepts
StereocenterChemistryMethyleneDiastereomerNuclear magnetic resonance spectroscopyMoleculeSulfoxideChemical shiftDeuteriumMethanolStereochemistryDimethyl sulfoxideProton NMROrganic chemistryEnantioselective synthesisCatalysisPhysical chemistryPhysicsQuantum mechanicsMolecular spectroscopy and chiralityAnalytical Chemistry and ChromatographyAxial and Atropisomeric Chirality Synthesis