Synthesis of Functionalized Tetrahydropyridines by SNCl4-mediated [4+2] Cycloaddition between Donor–Acceptor Cyclobutanes and Nitriles
Chem. Eur. J.
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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 via Lewis acid activation. Tetrahydropyridine derivatives were obtained in up to 91% yield from various aryl activated cyclobutane diesters and aliphatic or aromatic nitriles.
"This is the peer reviewed version of the following article: Wong, D., Wu, J., Bazinski, N., Koo, D., Vemula, N. & Pagenkopf, B. (2019). Synthesis of Functionalized Tetrahydropyridines by SnCl4-mediated [4+2] Cycloaddition between Donor–Acceptor Cyclobutanes and Nitriles. Chem. Eur. J. 10.1002/chem.201903833, which has been published in final form at https://onlinelibrary.wiley.com/doi/epdf/10.1002/chem.201903833. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions."