Resolution of 1-n-butyl-3-methyl-3-phospholene 1-oxide with TADDOL derivatives and calcium salts of O,O'-Dibenzoyl-(2R,3R)- or O,O'-di-p-toluoyl-(2R,3R)-tartaric acid

Chirality. 2014 Mar;26(3):174-82. doi: 10.1002/chir.22293. Epub 2014 Feb 8.

Abstract

The resolution methods applying (-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ("TADDOL"), (-)-(2R,3R)-α,α,α',α'-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol ("spiro-TADDOL"), as well as the acidic and neutral Ca(2+) salts of (-)-O,O'-dibenzoyl- and (-)-O,O'-di-p-toluoyl-(2R,3R)-tartaric acid were extended for the preparation of 1-n-butyl-3-methyl-3-phospholene 1-oxide in optically active form. In one case, the intermediate diastereomeric complex could be identified by single-crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by comparing the experimentally obtained and calculated CD spectra.

Keywords: CD spectroscopy; P-chirality; X-ray crystallography; absolute P-configuration; alkyl-3-phospholene 1-oxide; optical isomers; resolution methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calcium / chemistry*
  • Cyclic P-Oxides / analysis
  • Cyclic P-Oxides / chemistry*
  • Cyclic P-Oxides / isolation & purification*
  • Dioxolanes / chemistry*
  • Methanol / analogs & derivatives*
  • Methanol / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Organophosphorus Compounds / analysis
  • Organophosphorus Compounds / chemistry*
  • Organophosphorus Compounds / isolation & purification*
  • Salts / chemistry
  • Stereoisomerism
  • Tartrates / chemistry*

Substances

  • Cyclic P-Oxides
  • Dioxolanes
  • Organophosphorus Compounds
  • Salts
  • Tartrates
  • alpha,alpha,alpha',alpha'-tetraaryl-1,3-dioxolane-4,5-dimethanol
  • Calcium
  • tartaric acid
  • Methanol