Stereoselective synthesis of enamino ketones through an aza-Michael/hydrolysis cascade reaction
Related Experiment Video
Updated: Mar 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Hai-Lei Cui1, Li-Jie Peng, Hai-Lin Zhou
1International Academy of Targeted Therapeutics and Innovation, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing 402160, P.R. China. cuihailei616@163.com.
Abstract:
We have developed a mild, convenient and efficient synthesis of highly functionalized (Z)-β-enamino ketones from readily available 3,4-dihydroisoquinoline imines and ynones through an aza-Michael/hydrolysis cascade reaction. This method is also suitable for the preparation of (Z)-β-enamino esters using alkynoates as starting materials. Complex fully substituted pyrroles can be constructed from the obtained (Z)-β-enamino ketones. It is an attractive alternative approach for the preparation of highly functionalized enamino ketones, esters and pyrroles.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
09:14Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Conjugate Addition of Enolates: Michael Addition
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: Enamine Formation Mechanism
α-Alkylation of Ketones via Enolate Ions