Evaluation of the use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of secondary cyclohexenols

Abstract

The use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of isomeric mixtures of bicyclic and monocyclic secondary cyclohexenols was investigated. Synthesis, NMR and conformational analyses of the derivatives were performed and Gauge-Independent Atomic Orbital (GIAO) 1H NMR Boltzmann weighted average chemical shifts were computed. The studied methodology proved to be of practical value for most of the systems under study.