N-Arylcarbonylpseudoprolines as Tunable Chiral Derivatizing Agents for the Determination of the Absolute Configuration of Secondary Alcohols

Abstract

New chiral derivatizing agents, 3-arylcarbonyl-2,2-dimethyloxazolidine-4-carboxylic acids (N-arylcarbonylpseudoprolines), were prepared through a simple, short-step synthesis. The absolute configuration of secondary alcohols can be assigned on the basis of the NMR spectroscopic chemical shift difference between diastereomeric pseudoproline esters. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect.