Related Experiment Video
Updated: Jul 11, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Copper-Catalyzed Remote Enantioselective Sulfonylation of Yne-Allylic Esters with Sodium Sulfinates
Meng-Die Li1, Zi-Han Wang1, Hui Zhu1
1Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000, P. R. China.
Abstract:
Impressive progress has been made in the copper-catalyzed asymmetric propargylic substitution (APS) reaction, but its use in remote asymmetric yne-allylic substitution remains a challenging topic. Herein, we report the first remote enantioselective copper-catalyzed sulfonylation of yne-allylic esters with sodium sulfinates. The reaction is assumed to occur via a copper-vinylvinylidene species as the key reactive intermediate. The use of readily available starting materials, the mild reaction conditions, and the excellent regio-, enantio- and stereoselectivity, as well as broad substrate scope (>70 examples), show the practicality and attractiveness of this method.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Preparation and Reactions of Sulfides
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Acid Halides to Esters: Alcoholysis
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
α-Alkylation of Ketones via Enolate Ions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...