PHASE-TRANSFER SYNTHESIS OF OPTICALLY PURE OXETANES OBTAINED FROM 1,2,2-TRISUBSTITUTED 1,3-PROPANEDIOLS

XM HU, RM KELLOGG, Xianming Hu

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Abstract

Treatment of the 3-monomethanesulfonates of 1,2,2-trisubstituted 1,5-propanediols under phase-transfer conditions affords 2-aryl (or alkyl)-3,3-dialkyloxetanes. Twelve oxetanes have been obtained by this method; three of these oxetanes have been obtained enantiomerically pure as both enantiomers starting from the appropriate enantiomerically pure 1,3-diols. In these reactions the chiral center does not undergo inversion and the oxetanes have the same absolute configuration as the starting 1,3-diols.

Original languageEnglish
Pages (from-to)533-538
Number of pages6
JournalSynthesis-Stuttgart
Volume1995
Issue number5
DOIs
Publication statusPublished - May-1995

Keywords

  • OXETANES
  • 1,3-PROPANEDIOLS
  • MESYLATES
  • OPTICALLY PURE
  • PHASE-TRANSFER CATALYSIS
  • OXYGEN YLIDES
  • LITHIUM

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