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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

(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
JournalMolecules
Volume28
Issue number9
DOIs
Publication statusPublished - 1 May 2023

Keywords

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

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