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Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C3) Sequences: Scope, Limitation, and Computational Investigations

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posted on 12.07.2018, 00:00 by Riley H. Kaufman, Chunyin M. Law, Justin A. Simanis, Erica L. Woodall, Christian R. Zwick, Henry B. Wedler, Paul Wendelboe, Christopher G. Hamaker, John R. Goodell, Dean J. Tantillo, T. Andrew Mitchell
Oxidopyrylium-alkene [5 + 2] cycloaddition conjugate addition cascade (C3) sequences are described. Intramolecular cycloadditions involving terminal alkenes, enals, and enones were investigated. Substrates with tethers of varying lengths delivered five- and six-membered carbocycles and heterocycles thus demonstrating the scope and limitation of the cycloaddition–conjugate addition cascade. Several experiments and theoretical calculations provide evidence for the proposed mechanistic pathway.