New chemistry of chiral 1,3-dioxolan-4-ones

R Alan Aitken*, Lynn A. Power, Alexandra M. Z. Slawin

*Corresponding author for this work

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(2S,5S)-5-Phenyl-2-t-butyl-1,3-dioxolan-4-one, readily derived from mandelic acid, undergoes 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 (2S)-5-methylene-2-t-butyl-1,3-dioxolan-4-one, derived from lactic acid, has been further examined with 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.
Original languageEnglish
Article number3845
Number of pages18
Issue number9
Publication statusPublished - 1 May 2023


  • Dioxolanones
  • Michael addition
  • Diels–Alder reaction
  • Flash vacuum pyrolysis
  • X-ray structure


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