Synthesis of Functionalized Tetrahydropyridines by SnCl4-Mediated [4+2] Cycloaddition between Donor–Acceptor?Cyclobutanes and Nitriles |
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| Authors: | David Tong Jackie Wu Nathan Bazinski Donghyun Koo Naresh Vemula Prof?Dr Brian L Pagenkopf |
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| Institution: | Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, Ontario, N6A 5B7 Canada |
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| Abstract: | Cycloadditions of strained carbocycles promoted by Lewis acids are powerful methods to construct heterocyclic frameworks. In fact, the formal 3+2] cycloadditions of donor–acceptor (DA) cyclopropanes with nitriles has seen particular success in synthesis. In this work, we report on the first 4+2] cycloaddition of nitriles with DA cyclobutanes by Lewis acid activation. Tetrahydropyridine derivatives were obtained in up to 91 % yield from various aryl-activated cyclobutane diesters and aliphatic or aromatic nitriles. |
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| Keywords: | cycloaddition cyclobutane donor–acceptor systems nitrogen heterocycles strained molecules |
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