Related Experiment Video
Updated: Mar 31, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes
Kazuki Maeda1, Takuma Terada1, Takahiro Iwamoto1
1Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Abstract:
A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4 + 2] cycloaddition of N-tosylated α,β-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porphyrin complex to activate both the imino and carbonyl groups and (ii) the hydrophobic nature of the porphyrin ligand, which helps realize robust Lewis acidity in the dehydrative cycloaddition.
More Related Videos
10:51The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
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
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Electrophilic Addition to Alkynes: Hydrohalogenation