Synlett 1994; 1994(2): 95-104
DOI: 10.1055/s-1994-22753
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
22 March 2002 (online)

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