Related Experiment Video
Updated: Jan 10, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Asymmetric formal [1 + 2 + 2]-cycloaddition of diazoamides with enamines and carbonyl compounds
Shanliang Dong1, Minghan Yao2, Yunzhe Wang2
1School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, China.
Abstract:
Cycloaddition reaction offers an ideal and powerful method for the construction of cyclic structures with molecular complexity and diversity. The exploration of versatile synthons, especially in situ formed species, for the assembly of poly-functionalized heterocycles in one-pot is an intriguing and challenging area in synthetic chemistry from the perspective of atom economy and bond formation efficiency. Herein, we report an asymmetric formal [1 + 2 + 2]-cycloaddition of readily accessible diazoamides with enamines and carbonyl compounds. This cascade reaction involves a 1,3-dipolar cycloaddition of ketones/aldehydes with the key zwitterionic intermediate that generated in situ through an intermolecular metal carbene transfer to nucleophilic enamines, which offers a direct access to spiro-tetrahydrofurans containing four consecutive stereocenters in high yields and excellent enantioselectivity through chiral copper complex or chiral dirhodium carboxylates catalysis.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Aryldiazonium Salts to Azo Dyes: Diazo Coupling