Related Experiment Video
Updated: Sep 26, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Synthesis of α-C-Stereochemically Pure Secondary Sulfonamides
Vladyslav A Andriashvili1,2, Serhii Zhersh1,2, Andrey A Tolmachev1,2
1Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine, www.enamine.net.
Abstract:
A convenient "green" stereoretentive approach to sp3-enriched secondary sulfonamides bearing an asymmetric center at the α position to the sulfur atom is described. The method relies on the electrophilic amination of the corresponding stereochemically pure sulfinates with N-alkylhydroxylamine sulfonic acids (in turn easily prepared from N-alkylhydroxylamine and HSO3Cl). It is shown that the efficiency of the approach is governed mainly by steric factors; its tolerance to several functional groups (e.g., ether, phthalimide, or N-Boc carbamate) is also demonstrated.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Preparation and Reactions of Sulfides
Amines to Sulfonamides: The Hinsberg Test
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nomenclature of Secondary and Tertiary Amines
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview