Related Experiment Video
Updated: Aug 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Asymmetric Dihydroxylation-Based Kinetic Resolution of Allylic Amides Enabled by Noncovalent π-Interactions
Chengcheng Li1,2, Fumin Chen1,2, Qianqian Mu2
1School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China.
Abstract:
While Sharpless asymmetric dihydroxylation is widely utilized to convert various alkenes into diols with excellent enantioselectivies, kinetic resolution by means of this fundamental catalysis has generally proven to be ineffective. Here we report that, by relying on noncovalent π-interactions that purposely include the substrate's stereocenter in the corresponding catalyst-substrate interaction framework, AD-based kinetic resolution of allylic amides is realized. This method enables such versatile chiral building blocks to be easily accessed with excellent enantiomeric excesses (ee's).
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
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
α-Alkylation of Ketones via Enolate Ions
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Aldol Condensation with β-Diesters: Knoevenagel Condensation

