New synthetic approach to α-fluoro-β-arylvinyl sulfones and their application in Diels-Alder reactions |
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Authors: | Aleksey V Shastin Vasiliy M Muzalevskiy Roland Fröhlich |
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Institution: | a Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russia b Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, D-48149 Münster, Germany |
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Abstract: | A new pathway towards α-fluoro-β-arylvinyl sulfones was elaborated. The reaction of β-bromo-β-fluorostyrenes with sodium 4-methylphenylsulfinate proceeds with maximum 94:6 stereoselectivity and 72-90% yields. The formed α-fluoro-β-arylvinyl sulfones were found to be good dienophiles for Diels-Alder reactions with simple 1,3-dienes. From corresponding (E)-configured dienophiles and cyclopentadiene, cycloadducts bearing the fluorine substituent in exo-position were formed predominantly, while with diphenylisobenzofuran the products with endo-orientation of the fluorine were obtained as the major products. From these cycloadducts, as a proof of principle, p-toluenesulfinic acid was eliminated to give 2-fluoro-3-(4-nitrophenyl)norbornadiene, the formal 4+2]-cycloadduct of cyclopentadiene and 1-fluoro-2-(4-nitrophenyl)acetylene, or the corresponding diphenylisobenzofuran cycloadducts, respectively. This reaction was not successful when other β-hydrogen atoms are accessible for elimination. |
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Keywords: | Diels-Alder reaction Fluoroalkynes α-Fluoro-β-arylvinyl sulfones Fluoronorbornadienes Stereoselectivity Vinyl fluorides |
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