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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/116/03/0159-0162

    • Keywords

       

      Proline-catalysed ketol cyclization; template mechanism

    • Abstract

       

      A modified template mechanism based on modelling studies of energy minimised complexes is presented for the asymmetric proline-catalysed cyclization of triketones1,2 and3 to the 2S,3S-ketols1a,2a and3a respectively. The template model involves a three-point contact as favoured in enzyme-substrate interactions. Our minimisation studies are in agreement with the divergent behaviour of the 6,5-, 6,6-and 6,7-bicyclic systems. They support the high 93.4%ee observed with the 6,5-bicyclic ketol and the lower 73%ee found with the 6,6-bicyclic ketol. The calculations also explain the lack of asymmetric induction with the 6,7-bicyclic system

    • Author Affiliations

       

      R Malathi1 D Rajagopal2 Zoltan G Hajos3 4 S Swaminathan2

      1. Department of Crystallography and Biophysics, University of Madras, Chennai - 600 025, India
      2. Department of Organic Chemistry, University of Madras, Chennai - 600 025, India
      3. Hoffmann-La Roche Inc, Nutley, NJ - 07110, USA
      4. 802A, Pompton Road, Monroe Township, NJ - 08831-4234, USA
    • Dates

       
  • Journal of Chemical Sciences | News

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