Related Experiment Video
Updated: Jun 9, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective Intramolecular Oxidative Aminoacetoxylation from Aryl-Substituted Alkene via Chiral
Dongyuan Ju1, Jiaao Kang1, Zhiguang Song1
1State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, Jilin 130012, China.
Abstract:
Here, we describe an enantioselective intramolecular oxidative aminoacetoxylation reaction using a palladium catalyst and an aryl-substituted internal alkene compound as the substrate under mild conditions in several hours. The triazole-oxazoline ligand was selected for the asymmetric catalyst. A range of enantioenriched pyrrolidine-derived vicinal amino acetate compounds were synthesized, showing yields from 47% to 84%, diastereomer ratios from 57:43 to 95:5, and enantiomer excesses from 67% to 92%.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
α-Alkylation of Ketones via Enolate Ions
Radical Anti-Markovnikov Addition to Alkenes: Overview
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...
Regioselectivity of Electrophilic Additions-Peroxide Effect

