• Fulltext


        Click here to view fulltext PDF

      Permanent link:

    • 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

© 2021-2022 Indian Academy of Sciences, Bengaluru.