New chemistry of chiral 1,3-dioxolan-4-ones
MetadataShow full item record
Altmetrics Handle Statistics
Altmetrics DOI Statistics
(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.
Aitken , R A , Power , L A & Slawin , A M Z 2023 , ' New chemistry of chiral 1,3-dioxolan-4-ones ' , Molecules , vol. 28 , no. 9 , 3845 . https://doi.org/10.3390/molecules28093845
Copyright © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
DescriptionFunding: Authors thank the School of Chemistry for a studentship to L. A. P.
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.