Absolute configuration of ketone cyanohydrins by 1H NMR: the special case of polar substituted tertiary alcohols

Org Lett. 2009 Jan 1;11(1):53-6. doi: 10.1021/ol8023314.

Abstract

The absolute configuration of ketone cyanohydrins can be assigned from analysis of the 1H NMR spectra of the corresponding (R)- and (S)-MPA ester derivatives and use of delta delta(RS) signs. This is an application of the NMR methodology for stereochemical assignment to tertiary alcohols possessing polar groups as substituents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Nitriles / chemistry*
  • Protons
  • Reference Standards
  • Stereoisomerism

Substances

  • Alcohols
  • Ketones
  • Nitriles
  • Protons
  • cyanohydrin