Related Experiment Video
Updated: Sep 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium-Catalyzed Asymmetric Aminomethylative Pyridonation of Conjugated Dienes
Guoqing Yang1, Song Liu2, Hanmin Huang1
1State Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China.
Abstract:
A novel palladium-catalyzed asymmetric aminomethylative pyridonation of conjugated dienes with N,O-acetals and 2-hydroxypyridines was established, which provided a direct and reliable method for the synthesis of a wide range of γ-aminated N-substituted 2-pyridones with good to excellent enantioselectivities. The simple BF3 was identified as an effective cocatalyst to improve the reaction efficiency, and DFT calculations revealed that proton transfer between the aminomethylated allylic palladium species and 2-hydroxypyridine promoted by BF3 is crucial for obtaining good reactivity.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...