Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C<sup>3</sup>) Sequences: Scope, Limitation, and Computational Investigations
- Riley H. Kaufman (5561657)
- Chunyin M. Law (5561660)
- Justin A. Simanis (1939168)
- Erica L. Woodall (1939162)
- Christian R. Zwick (5561663)
- Henry B. Wedler (1610557)
- Paul Wendelboe (5561666)
- Christopher G. Hamaker (1939171)
- John R. Goodell (1317582)
- Dean J. Tantillo (1312941)
- T. Andrew Mitchell (1939165)
Publication date
July 2018
DOIAbstract
Oxidopyrylium-alkene [5 + 2] cycloaddition conjugate addition cascade (C<sup>3</sup>) 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
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