Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes
Ferrocenyl thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dim...
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Beilstein-Institut
2020-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.16.109 |
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| author | Grzegorz Mlostoń Mateusz Kowalczyk André U. Augustin Peter G. Jones Daniel B. Werz |
| author_facet | Grzegorz Mlostoń Mateusz Kowalczyk André U. Augustin Peter G. Jones Daniel B. Werz |
| author_sort | Grzegorz Mlostoń |
| collection | DOAJ |
| description | Ferrocenyl thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone. |
| first_indexed | 2024-12-13T13:14:59Z |
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| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T13:14:59Z |
| publishDate | 2020-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4a58a4fe44734cb585e585cc26a3f7472022-12-21T23:44:34ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-06-011611288129510.3762/bjoc.16.1091860-5397-16-109Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanesGrzegorz Mlostoń0Mateusz Kowalczyk1André U. Augustin2Peter G. Jones3Daniel B. Werz4University of Łódź, Department of Organic & Applied Chemistry, Tamka 12, 91-403 Łódź, PolandUniversity of Łódź, Department of Organic & Applied Chemistry, Tamka 12, 91-403 Łódź, PolandTechnische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany,Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, GermanyTechnische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany,Ferrocenyl thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.https://doi.org/10.3762/bjoc.16.109[3 + 2]-cycloaddition reactionsdonor–acceptor cyclopropanesferrocenyl thioketonessulfur heterocyclestetrahydrothiophenes |
| spellingShingle | Grzegorz Mlostoń Mateusz Kowalczyk André U. Augustin Peter G. Jones Daniel B. Werz Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes Beilstein Journal of Organic Chemistry [3 + 2]-cycloaddition reactions donor–acceptor cyclopropanes ferrocenyl thioketones sulfur heterocycles tetrahydrothiophenes |
| title | Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes |
| title_full | Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes |
| title_fullStr | Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes |
| title_full_unstemmed | Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes |
| title_short | Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes |
| title_sort | ferrocenyl substituted tetrahydrothiophenes via formal 3 2 cycloaddition reactions of ferrocenyl thioketones with donor acceptor cyclopropanes |
| topic | [3 + 2]-cycloaddition reactions donor–acceptor cyclopropanes ferrocenyl thioketones sulfur heterocycles tetrahydrothiophenes |
| url | https://doi.org/10.3762/bjoc.16.109 |
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