Related Experiment Video
Updated: Jan 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Polarity-Reversed Addition of Enol Ethers to Imines under Visible Light: Redox-Neutral Access to Azide-Containing
Sen Yang1, Shuangyu Zhu1, Dengfu Lu1
1School of Chemistry and Chemical Engineering , Huazhong University of Science and Technology , 1037 Luoyu Road , Wuhan , Hubei 430074 , China.
Abstract:
A three-component and polarity-reversed addition cascade with a glyoxylate-based imine, an enol ether, and TMSN3 was established for the construction of γ-azido amino acids under visible light. This transformation features mild and redox-neutral conditions, affording a series of amino esters with excellent chemoselectivity. Preliminary mechanistic studies revealed that the addition of an oxyalkyl radical to imine is likely the rate-determining step. The obtained azido-containing amino esters could be successfully converted to various valuable building blocks.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Related Concept Videos
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
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...
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Conjugate Addition of Enolates: Michael Addition