New Chemistry of Chiral 1,3-Dioxolan-4-Ones
Abstrak
(2<i>S</i>,5<i>S</i>)-5-Phenyl-2-<i>t</i>-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<i>S</i>)-5-methylene-2-<i>t</i>-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.
Topik & Kata Kunci
Penulis (3)
R. Alan Aitken
Lynn A. Power
Alexandra M. Z. Slawin
Akses Cepat
- Tahun Terbit
- 2023
- Sumber Database
- DOAJ
- DOI
- 10.3390/molecules28093845
- Akses
- Open Access ✓