[3+2]-Cycloaddition reactions of gem-difluorocyclopropenes with azomethine ylides – access to novel fluorinated scaffolds
Donnelly, Kian and Singh, Amritpal and Tuttle, Tell and Baumann, Marcus (2023) [3+2]-Cycloaddition reactions of gem-difluorocyclopropenes with azomethine ylides – access to novel fluorinated scaffolds. Chemistry - A European Journal, 29 (54). e202301861. ISSN 1521-3765 (https://doi.org/10.1002/chem.202301861)
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Abstract
The introduction of fluorinated moieties into drugs as well as the increase of their overall three-dimensionality have become key strategies amongst medicinal chemists to generate sets of compounds with favorable drug-like properties. However, the introduction of fluorinated cyclopropane ring systems which combines both strategies is not widely exploited to date. This paper reports synthetic strategies exploiting the reactivity of gem-difluorocyclopropenes in dipolar cycloaddition reactions with azomethine ylides to afford sets of new fluorine-containing 3-azabicyclo[3.1.0]hexanes. In addition, the unexpected formation of complex trifluorinated scaffolds arising from proline esters and gem-difluorocyclopropenes is highlighted along with computational studies to elucidate the underlying mechanism. This study presents new avenues towards pharmaceutically relevant fluorinated 3-azabicyclo[3.1.0]hexanes that are accessible via robust and short synthetic sequences.
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Item type: Article ID code: 86938 Dates: DateEvent26 September 2023Published18 August 2023Published Online4 July 2023Accepted10 June 2023SubmittedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > BionanotechnologyDepositing user: Pure Administrator Date deposited: 12 Oct 2023 08:48 Last modified: 11 Oct 2024 00:35 URI: https://strathprints.strath.ac.uk/id/eprint/86938