A practical and efficient method for the resolution of 3-phospholene 1-oxides via coordination complex formation

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25 Citations (Scopus)

Abstract

A simple, efficient, and economical method based on the combination of the exceptional behavior of o,o′-dibenzoyl- or o,o′-di-p-toluyl-(2R,3R)- tartaric acid in chiral recognition processes, and the coordination ability of calcium or magnesium ion was developed for the resolution of phospholene oxides 1. The calcium or magnesium salt of (2)-o,o′-dibenzoyl-(2R,3R)-tartaric acid 2,4-6 or calcium hydrogen (2)-o,o′-di-ptoluyl-( 2R,3R)-tartrate 3 may form crystalline diastereomeric coordination complexes with the appropriate antipode of substituted 3-phospholene oxides 1 that makes possible efficient resolutions. Optically active phospholene oxides 1 were prepared directly by simply crystallization and digestion of the corresponding diastereomeric complexes so formed. Thermal behavior of the crystalline diastereomeric complexes was studied by simultaneous TG/DTA. The novel method may be of more general value in respect of the resolution of tertiary phosphine oxides.

Original languageEnglish
Pages (from-to)699-705
Number of pages7
JournalChirality
Volume22
Issue number7
DOIs
Publication statusPublished - Jul 1 2010

Keywords

  • Coordinative resolution
  • P-chiral phospholene oxides
  • Solvent dependence
  • Tartaric acid derivatives

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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