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Updated: Oct 9, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Solvent Effects and Mechanistic Studies for Re2O7-Catalyzed Allylative Annulation Reactions
Shelby M Anderson1, Marcus D Van Engen1, Paul E Floreancig1
1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Abstract:
The sequence of allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition results in the formation of a ring while serving as a fragment-coupling and stereocenter-generating reaction. Successful applications of these processes require a balancing of the kinetics of numerous productive and unproductive steps. This work describes the manner in which solvent changes can be used to expand the scope and change the stereochemical outcomes of these processes. Mechanistic studies provide greater insight into the nuances of the transformations and the reactive species that are generated.
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