The application of (S)-1,10-binaphthyl-2,20-diol as NMR chiral solvating agent (CSA) for omeprazole, and three of its analogs (lanso-, panto-, and rabe-prazole) was investigated. The formation of diastereomeric host–guest complexes in solution between the CSA and the racemic substrates produced sufficient NMR signal splitting for the determination of enantiomeric excesses by Hor F-NMR spectroscopy. Using of hydrophobic deuterated solvents was mandatory for obtaining good enantiodiscrimination, thus suggesting the importance of intermolecular hydrogen bonds in the stabilization of the complexes. The method was applied to the fast quantification of the enantiomeric purity of in-process samples of S-omeprazole. Chirality 00:000–000, 2009. VC 2009

The assignment of absolute configuration by NMR

New chiral anisotropic reagents for determining the absolute configuration of carboxylic acids

A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates

This article describes the application of the modified Mosher’s method to a variety of natural products possessing a secondary alcohol for determining their absolute configuration. The method is ge...

The Modified Mosher’s Method and the Sulfoximine Method

Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, methoxy-(2-naphthyl)acetic acid

Yukiko Kan

Papers

New chiral anisotropic reagents, NMR tools to elucidate the absolute configurations of long-chain organic compounds