Bicyclic β-lactones via intramolecular NCAL reactions with cinchona alkaloids: Effect of the C9-substituent on enantioselectivity and catalyst conformation

  • Cortez G
  • Oh S
  • Romo D
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Abstract

C9-Acylated cinchona alkaloids promote an intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reaction leading to optically active bicyclic β-lactones. A mechanistic scheme is proposed for this catalytic, asymmetric process. Only small variations in enantioselectivity were observed for a variety of esters, a carbamate, and a carbonate at the C9 position of quinidine. A combination of coupling constants (3JH8,H9) and nOe data was used to assign predominant solution conformations for these derivatives. Interestingly, a more rigid quinidine derivative gave a complete reversal in the sense of enantioselection.

Author-supplied keywords

  • 2-oxetanones
  • Aldol-lactonizations
  • Asymmetric nucleophilic catalysis
  • Coupling constants
  • Nuclear Overhauser effect

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Authors

  • G. S. Cortez

  • S. H. Oh

  • D. Romo

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