Related Experiment Video
Updated: Apr 13, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Nitrene Transfer-Triggered Novel Oxa-Pictet-Spengler Reaction: A Versatile Approach to Amino-Functionalized
Yuchen Yang1, Xu Liu1, Teng Sun1
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, Department of Chemistry, East China Normal University, Shanghai, China.
None:
A novel nitrene transfer-triggered oxa-Pictet-Spengler reaction has been developed for the efficient synthesis of amino-functionalized dihydropyran scaffolds under rhodium catalysis. With Rh2(TPA)4 as the optimal catalyst, the reaction exhibits broad substrate scope, delivering the corresponding products (20 examples) in good yields (32%-89%). Gram-scale synthesis proceeds smoothly, and facile deprotection of the Ns group affords primary amines in good efficiency. Kinetic isotope effect studies (kH/kD = 2.2) reveal that C-H bond cleavage is involved in the rate-determining step. This work provides a versatile strategy for accessing amino-dihydropyran scaffolds, merging nitrene transfer with the oxa-Pictet-Spengler reaction for the first time.
More Related Videos
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

