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Updated: Feb 27, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective Oxidative (4+3) Cycloadditions between Allenamides and Furans through Bifunctional
Laura Villar1, Uxue Uria1, Jose I Martínez1
1Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080, Bilbao, Spain.
Abstract:
BINOL-based N-trifluoromethanesulfonyl phosphoramides catalyze the enantioselective (4+3) cycloaddition between furans and oxyallyl cations, the latter being generated in situ by oxidation of allenamides. The chiral organic phosphoramide counteranion is proposed to engage in the activation of the oxyallyl cation intermediate through cooperative hydrogen-bonding and ion-pairing interactions, enabling an efficient chirality transfer that provide the final adducts with high diastereo- and enantioselectivities. Remarkably, the reaction shows a wide substrate scope that includes a variety of substituted allenamides and furans.
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