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

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.