Synthesis of Functionalized Tetrahydropyridines by SnCl4‐Mediated Cycloaddition between Donor–AcceptorCyclobutanes and Nitriles
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] c...
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Veröffentlicht in: | Chemistry : a European journal 2019-12, Vol.25 (67), p.15244-15247 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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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ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201903833 |