Triflic Acid-promoted Regio and Stereoselective Synthesis of Polyfunctionalized Enaminones From Dibenzylidene Ketones and Organic Azides
Year: 2024
Type: article
Abstract: A stereoselective synthesis of α-aryl Z enaminones was developed by TfOH-promoted condensation of dibenzylidene ketones with organic azides. The cascade reactions involve the sequence of 1,3-dipolar cycloaddition of alkyl azides with the enone, aziridine formation, and 1,2-aryl migration via phenonium ion, whose stereochemical control by a strong N–H…O=C intramolecular hydrogen bond affords Z isomer exclusively. The readily available starting materials and ease of handling of TfOH are experimental advantages that give diversely substituted enaminones with total control of functionalization along the N–C=C–C=O conjugated system.
Source: Química Nova
Authors: Lucas Souza Prates, Silvio Cunha
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $330
OpenAlex ID: W4403541348