title: Gosteli-Claisen rearrangement of propargyl vinyl ethers: cascading molecular rearrangements.
abstract: The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli-Claisen rearrangement triggers downstream transformations that cascade from initially formed γ-allenyl α-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed.
authors.affiliation: Fakultät Chemie, Technische Universität Dortmund, 44227 Dortmund, Germany.
authors.forename: Annika
authors.initials: A
authors.lastname: Gille
authors.forename: Julia
authors.initials: J
authors.lastname: Rehbein
authors.forename: Martin
authors.initials: M
authors.lastname: Hiersemann