Enantioselective Synthesis of Atropisomers by Oxidative Aromatization with Central-to-Axial Conversion of Chirality

Author:

Lemaitre Clément1,Perulli Stefania2,Quinonero Ophélie1,Bressy Cyril1,Rodriguez Jean1,Constantieux Thierry1,García Mancheño Olga2ORCID,Bugaut Xavier13

Affiliation:

1. Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, 13397 Marseille, France

2. Organic Chemistry Institute, University of Münster, Corrensstraße 36/40, 48149 Münster, Germany

3. Université de Strasbourg, Université de Haute-Alsace, CNRS, LIMA, UMR 7042, 67000 Strasbourg, France

Abstract

Atropisomers are fascinating objects of study by themselves for chemists but also find applications in various sub-fields of applied chemistry. Obtaining them in enantiopure form is far from being a solved challenge, and the past decades has seen a surge of methodological developments in that direction. Among these strategies, oxidative aromatization with central-to-axial conversion of chirality has gained increasing popularity. It consists of the oxidation of a cyclic non-aromatic precursors into the corresponding aromatic atropisomers. This review proposes a critical analysis of this research field by delineating it and discussing its historical background and its present state of the art to draw potential future development directions.

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Reference149 articles.

1. LX.—The molecular configurations of polynuclear aromatic compounds. Part V. The identity of the nitration products derived from 2:7- and 4:5-dinitrophenanthraquinones;Christie;J. Chem. Soc. Trans.,1922

2. Recent Advances in Atropisomerism;Allinger;Topics in Stereochemistry,2007

3. Entropic factors are generally small for rotations around a bond, and can be neglected. As a consequence, barriers to rotation can be seen as temperature-independent.

4. Nonbiaryl and Heterobiaryl Atropisomers: Molecular Templates with Promise for Atropselective Chemical Transformations;Kumarasamy;Chem. Rev.,2015

5. Enantioselective syntheses of atropisomers featuring a five-membered ring;Bonne;Chem. Commun.,2017

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