Issue 29, 2021

Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability

Abstract

The preparation of a series of novel homochiral atropisomeric sulfanyl- and sulfoxide-substituted naphthyltriazoles is described. The triazolization methodology used presents a new way towards novel and highly stable 1,2,3-triazole-based atropisomers, and introduces a new and complementary synthetic pathway towards 4-sulfanyl substituted 1,2,3-triazoles. Starting from sulfanyl-substituted naphthyl ketones, enantiopure amines, and 4-nitrophenyl azide, a collection of 16 sulfanyl-substituted naphthyltriazoles were obtained via the triazolization reaction in which the homochiral diastereomers are readily isolated. Subsequent monooxidation results in the preparation of several sulfoxide-substituted naphthyltriazoles. The absolute configuration of a set of diastereomeric sulfanyl- and sulfoxide-appended naphthyltriazoles was deduced via X-ray crystallography. Furthermore, the conformational stability of the atropisomers was determined experimentally, and further confirmed and analyzed with the aid of computational DFT calculations.

Graphical abstract: Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability

Supplementary files

Article information

Article type
Paper
Submitted
22 Apr 2021
Accepted
05 Jul 2021
First published
05 Jul 2021

Org. Biomol. Chem., 2021,19, 6521-6526

Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability

R. Vroemans, S. R. Ribone, J. Thomas, L. Van Meervelt, T. Ollevier and W. Dehaen, Org. Biomol. Chem., 2021, 19, 6521 DOI: 10.1039/D1OB00784J

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