Related Experiment Video
Updated: Aug 17, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
The first regioselective alpha-deprotonation and functionalization of allenamides. An application in intramolecular
1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Abstract:
[rection: see text] The first regioselective alpha-deprotonation and functionalization of electron-deficient allenamines are described here. The acidities of alpha- and gamma-allenic protons of these allenamides are readily differentiated using strong bases, thereby allowing regioselective substitutions at either the alpha- or gamma-allenic position. A specific synthetic application of the novel alpha-substituted allenamides in intramolecular Pauson-Khand-type cycloadditions is also described here.
Related Concept Videos
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
α-Alkylation of Ketones via Enolate Ions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

