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Synlett 2001; 2001(1): 0061-0064
DOI: 10.1055/s-2001-9730
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Chiral Oxazaborolidinone-Mediated Enantioselective Ring-Cleavage Reaction of a Mixture of Diastereomeric 1,3-Dioxolane Acetals: Application to Asymmetric Desymmetrization of meso-1,2-Diols

Toshiro Harada* , Hideki Yamanaka, Akira Oku
  • *Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan; E-mail: harada@chem.kit.ac.jp
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Publication Date:
31 December 2001 (online)

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Ring-cleavage reaction of a mixture of diastereomeric dioxolane acetals syn- and anti-1b-e proceeds in an enantiodifferentiating manner in the presence of chiral Lewis acid 2. The reaction is utilized as a key step in asymmetric desymmetrization of meso-1,2-diols.

asymmetric synthesis - acetals - cleavage - diols - Lewis acids

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