Asymmetric Dearomative (3+2)-Cycloaddition Involving Nitro-Substituted Benzoheteroarenes under H-Bonding Catalysis |
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| Authors: | Maciej Saktura,Anna Skrzyń ska,Sebastian Frankowski,Sylwia Wó dka,Ł ukasz Albrecht |
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| Affiliation: | Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland; (M.S.); (S.F.); (S.W.) |
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| Abstract: | In our studies, the organocatalytic 1,3-dipolar cycloaddition between 2-nitrobenzofurans or 2-nitrobenzothiophene and N-2,2,2-trifluoroethyl-substituted isatin imines has been developed. The reaction has been realized by employing bifunctional organocatalysis, with the use of squaramide derivative being crucial for the stereochemical efficiency of the process. The usefulness of the cycloadducts obtained has been confirmed in selected transformations, including aromative and non-aromative removal of the nitro group. |
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| Keywords: | organocatalysis CADA reactions dearomative (3+2)-cycloaddition 2-nitrobenzofurans azomethine ylides |
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