A RAPID ASSAY FOR THE ENANTIOMERIC PURITY OF SECONDARY ALCOHOLS USING 4S,5R-4-METHYL,5-PHENYL-1,3,2-OXAZABOROLIDINE (EPHEDRINEBORANE)

JM BROWN*, SW LEPPARD, GC LLOYD-JONES, Guy Lloyd-Jones

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Reaction of the title compound with a series of racemic and optically enriched secondary alcohols in C7D8 solution at 20-degrees-C leads to rapid formation of the corresponding borate. The N-CH3 protons of the ephedrine moiety, and frequently other resonances, were generally resolved in the H-1 NMR spectrum. permitting an estimation of the enantiomeric purity of the alcohol.

Original languageEnglish
Pages (from-to)261-266
Number of pages6
JournalTetrahedron: Asymmetry
Volume3
Issue number2
Publication statusPublished - 1992

Keywords

  • GAS-CHROMATOGRAPHIC SEPARATION
  • LANTHANIDE SHIFT-REAGENTS
  • FREE STATIONARY PHASES
  • ABSOLUTE-CONFIGURATION
  • O-METHYLMANDELATE
  • CHEMICAL-SHIFTS
  • DERIVATIVES
  • RESOLUTION
  • ASSIGNMENT
  • ESTERS

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