- Copper-catalyzed regioselective synthesis of (E)-β-fluorovinyl sulfones
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Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed (E)-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and E/Z selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related Z isomers. These new products may find interesting applications, given the versatility of vinyl sulfones in chemical synthesis and the unique properties of vinyl fluorides in biological settings.
- Román, Raquel,Barrio, Pablo,Mateu, Natalia,Sedgwick, Daniel M.,Fustero, Santos
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- Approaches to 2,6-Diaryl-3,7-DioxabicycloOctane Lignans via Asymmetric Synthesis of Dihydro- and Tetrahydro-furan Derivatives
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Cyclisation of chiral non-racemic phenylsulphonylvinyl epoxy ethers, produced using the Sharpless epoxidation reaction, has been used to prepare a series of enantiomerically enriched 2-aryl-4-(α-hydroxybenzyl)-4,5-dihydrofuran derivatives.Reduction of these compounds using triethylsilane and BF3-diethyl ether gave the corresponding tetrahydrofuran derivatives stereoselectively.Attempts to convert either the dihydro- or tetrahydro-furan derivatives into lignans belonging to the 2,6-diaryl-3,7-dioxabicyclooctane series so far proved unsuccessful.
- Pelter, Andrew,Ward, Robert S.,Little, Gillian M.
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p. 2775 - 2790
(2007/10/02)
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