Related Experiment Video
Updated: Apr 2, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Photoinduced Palladium Catalysis Enables Dynamic Kinetic Asymmetric Allylic Imidation
Runquan Kang1, Weiwei Jin1, Xinru Zhang2
1State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Abstract:
Palladium (Pd)-catalyzed dynamic kinetic asymmetric transformation (DYKAT) provides a powerful approach to enantiomerically enriched molecules. Although well-established for monosubstituted and symmetric 1,3-disubstituted allylic substrates, the DYKAT of unsymmetrical 1,3-disubstituted systems remains a substantial challenge, with few general solutions reported. Here, we present a photoinduced Pd-catalyzed DYKAT that enables highly regio- and enantioselective imidation of unsymmetrical 1,3-disubstituted allylic electrophiles, including allyl esters, vinyl epoxides, and vinyl carbonates. This method delivers chiral allylamines and amino alcohols with up to >20:1 regioselectivity ratio and up to 99% enantiomeric excess. Mechanistic investigations reveal that visible-light excitation promotes rapid interconversion of two diastereomeric π-allyl Pd(II) intermediates. This process involves a key equilibrium between a Pd species and an allyl radical, which is essential for achieving enantioconvergent conversion under mild conditions.
More Related Videos
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
α-Alkylation of Ketones via Enolate Ions
Radical Anti-Markovnikov Addition to Alkenes: Overview