Jump to main content
Jump to site search


Experimental and computational evidence on gold-catalyzed regioselective hydration of phthalimido-protected propargylamines: an entry to β-amino ketones

Author affiliations

Abstract

The results of our investigations on the Au-catalyzed regioselective hydration reaction of both alkyl- and aryl-substituted N-propargyl phthalimides directed to the selective formation of the corresponding β-phthalimido ketones are described. Experimental data, in particular the observed regioselectivity, have been qualitatively supported by quantum-chemical calculations carried out on model systems in the framework of Density Functional Theory (DFT) followed by quantum theory of atoms in molecules (QTAIMS). Our results suggest that the electronic features of the initial adduct between the propargyl triple bond and the Au(I) catalyst, in particular the character of the gold-triple bond interaction, are essential for the observed regioselectivity. Other effects, such as the presence of the solvent and the formation of a H-bond between the water molecule and the phthalimido moiety, although apparently irrelevant for the regioselectivity, have proven to be kinetically and catalytically rather important.

Graphical abstract: Experimental and computational evidence on gold-catalyzed regioselective hydration of phthalimido-protected propargylamines: an entry to β-amino ketones

Back to tab navigation

Supplementary files

Article information


Submitted
03 Aug 2020
Accepted
05 Oct 2020
First published
05 Oct 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Experimental and computational evidence on gold-catalyzed regioselective hydration of phthalimido-protected propargylamines: an entry to β-amino ketones

V. Marsicano, A. Arcadi, M. Aschi and V. Michelet, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01598A

Social activity

Search articles by author

Spotlight

Advertisements