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Synthesis 1995; 1995(5): 533-538
DOI: 10.1055/s-1995-3939
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Phase-Transfer Synthesis of Optically Pure Oxetanes Obtained from 1,2,2-Trisubstituted 1,3-Propanediols

Hu Xianming, Richard M. Kellogg*
  • *Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax +31(50)634296; E-mail kellogg@chem.rug.nl
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Publication History

Publication Date:
31 December 2000 (online)

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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.

oxetanes - 1,3-propanediols - mesylates - optically pure - phase-transfer catalysis

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