Chiral organic stereochemistry: Chiral HPLC, chiral auxiliaries, CD spectroscopy, X-ray crystallography, and light-powered chiral molecular motors

Chirality. 2022 Feb;34(2):253-294. doi: 10.1002/chir.23372. Epub 2021 Nov 15.

Abstract

In the studies of chiral organic stereochemistry, it is important to use enantiopure compounds. For this purpose, the chiral HPLC (High-Pressure Liquid Chromatography) columns containing chiral stationary phases were invented by Y. Okamoto and coworkers for enantio-separating various racemic compounds. In addition, the use of chiral auxiliaries is also useful for preparing enantiopure compounds and also for determining their absolute configurations, where covalent-bonded diastereomers are separated by HPLC on silica gel. In this review article, these HPLC methods will be discussed together with the applications to some interesting organic compounds including light-powered chiral molecular motors.

Keywords: (+)-poly(triphenylmethyl methacrylate); (R)-(−)-2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid); (−)-camphor-sultam dichlorophthalic acid (CSDP acid); 1H NMR diamagnetic anisotropy method; CD exciton chirality method; cellulose tris(3,5-dimethylphenylcarbamate); π-Electron SCF-CI-DV MO method.

Publication types

  • Review

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Crystallography, X-Ray
  • Silica Gel
  • Spectrum Analysis
  • Stereoisomerism*

Substances

  • Silica Gel