A novel method for the determination of stereochemistry in six-membered chairlike rings using residual dipolar couplings

J Org Chem. 2003 Mar 7;68(5):1786-95. doi: 10.1021/jo020670i.

Abstract

A novel method for the determination of the relative stereochemistry of six-membered chairlike ring molecules by residual dipolar couplings is presented. C-H residual dipolar couplings were used to investigate the relative stereochemistry of 4,6-O-ethylidene-d-glucopyranose. For this and similar systems it is not necessary to acquire redundant dipolar couplings and to calculate the orientation order tensor. The presented methodology is a paradigmatic leap for the determination of the relative stereochemistry or remote stereochemistry in this kind of fused ring system. Residual dipolar coupling data were collected by 1D and 2D direct-measurement heteronuclear multiple quantum coherence (HMQC) spectroscopy. It was demonstrated that direct measurement of HMQC was quick and accurate for small molecules at natural abundance.

MeSH terms

  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Heterocyclic Compounds / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Heterocyclic Compounds