Flexible access to 2,3,5,6-tetrasubstituted dehydropiperidines by Ni- or Co-catalyzed site-selective cross-coupling using Vilsmeier-Haack-derived α-chloro-β-formyltetrahydropyridines
Department or Administrative Unit
A flexible and cost-effective method for the highly functional group-compatible and site-selective cross-coupling of readily affordable α-chloro-β-formyltetrahydropyridines has been developed, under nickel or cobalt catalysis, leading to the rapid synthesis of 2,3,5,6-tetrasubstituted dehydropiperidines bearing α-amino allylic stereocenters. Cobalt-catalyzed reductive cross-coupling of chloro enaminals with electronically-diverse bromostyrenes as coupling partners proceeds in good yields and with high E/Z selectivity to afford Diels-Alder-suitable cross-conjugated 1,3-dienes.
Farah, A. O., Archibald, R., Rodriguez, M. J., Moreno, A., Dondji, B., & Beng, T. K. (2018). Flexible access to 2,3,5,6-tetrasubstituted dehydropiperidines by Ni- or Co-catalyzed site-selective cross-coupling using Vilsmeier-Haack-derived α-chloro-β-formyltetrahydropyridines. Tetrahedron Letters, 59(38), 3495–3498. https://doi.org/10.1016/j.tetlet.2018.08.023
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