AI Article Synopsis
- The study focuses on a method for functionalizing β-CFH-1,3-enynes with nucleophiles through base-mediated reactions, yielding terminal monofluoroalkenes with an alkynyl group in good yields and selectivities.
- The mixtures produced can be effectively separated using flash chromatography, leading to stereoisomerically pure monofluoroenynes.
- Further modifications of these monofluoroenynes were conducted, demonstrating the ability to create a variety of different molecular structures, with computational studies explaining the observed diastereoselectivity.
Article Abstract
The base-mediated allylic defluorinative functionalization of β-CFH-1,3-enynes with nucleophiles is described, affording terminal monofluoroalkenes bearing an alkynyl group in synthetically useful yields and / selectivities. Importantly, the resultant / mixture could be separated by flash chromatography in all cases; thus, stereoisomerically pure monofluoroenynes were obtained. Postsynthetic modifications of the synthesized monofluoroenynes were also accomplished to access diverse molecular structures. Computational studies disclosed the origin of the diastereoselectivity.
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| http://dx.doi.org/10.1021/acs.orglett.4c02874 | DOI Listing |
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