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Synlett 1994; 1994(2): 95-104
DOI: 10.1055/s-1994-22753
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Enantiodifferentiating Transformation of Prochiral Polyols by Using Menthone as Chiral Template

Toshiro Harada* , Akira Oku
  • *Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606, Japan
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Publication Date:
22 March 2002 (online)

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Enantiogroup differentiating transformation of prochiral polyols which affords versatile chiral building blocks was developed by using menthone as a chiral template. Several important structural features of menthonides are described in connection with the origin of the stereoselectivity of the enantiodifferentiating transformation. Application to the stereocontrol of multi-stereogenic centers is also described. 1. Introduction 2. Structural Features of Spiroacetals Derived from Menthone 3. Enantiodifferentiating Transformation of Prochiral Diols 4. Resolution and Absolute Configuration Determination of 1,3-Alkanediols 5. Enantiodifferentiating Transformation of Polyols 5.1 Stereocontrol by Intramolecular van der Waals Attractive Interaction 5.2 Convergent Asymmetric Synthesis of Ansa Chain of Rifamycin S 6. Conclusion