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New Chemistry of Chiral 1,3-Dioxolan-4-Ones.

R Alan AitkenLynn A PowerAlexandra M Z Slawin
Published in: Molecules (Basel, Switzerland) (2023)
(2 S ,5 S )-5-Phenyl-2- t -butyl-1,3-dioxolan-4-one, readily derived from mandelic acid, undergoes the Michael addition to butenolide and 4-methoxy-β-nitrostyrene with the absolute configuration of the products confirmed by X-ray diffraction in each case. In the former case, thermal fragmentation gives the phenyl ketone, thus illustrating use of the dioxolanone as a chiral benzoyl anion equivalent. The Diels-Alder cycloaddition chemistry of (2 S )-5-methylene-2- t -butyl-1,3-dioxolan-4-one, derived from lactic acid, has been further examined with the X-ray structures of four adducts determined. In one case, thermal fragmentation of the adduct gives a chiral epoxy ketone resulting from the dioxolanone acting as a chiral ketene equivalent, while in others the products give insight into the mechanism of the dioxolanone fragmentation process.
Keyphrases
  • ionic liquid
  • capillary electrophoresis
  • high resolution
  • lactic acid
  • magnetic resonance imaging
  • electron microscopy
  • drug discovery
  • mass spectrometry
  • dual energy