Related Experiment Video
Updated: Mar 3, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Carbon-Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols
Barry M Trost1, Jacob S Tracy1
1Department of Chemistry, Stanford University , 333 Campus Drive, Stanford, California 94305, United States.
Abstract:
A vanadium catalyzed 1,3-rearrangement of allenols to form transient vanadium enolates that selectively couple with electrophilic nitrogen sources is reported even in the presence of competing simple protonation and Alder-ene pathways. Hydrazine products can be cyclized in a 6-endo-trig fashion which, upon reductive cleavage of the N-N bond, yield 1,4-diamines. Additionally, cleavage of the N-N bond before cyclization can be achieved to form β-hydroxy amines, a common structural motif of biologically active compounds.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
C–C Bond Formation: Aldol Condensation Overview
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Nonenolizable Aldehydes to Acids and Alcohols: The Cannizzaro Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

