Phase-transfer synthesis of optically pure oxetanes obtained from 1,2,2-trisubstituted 1,3-propanediols

Article abstract of DOI:10.1055/s-1995-3939

Treatment of the 3-monomethanesulfonates of 1,2,2-trisubstituted 1,3-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.