Issue 11, 2018

Stereoselective arene formation

Abstract

While aromatic hydrocarbons are ubiquitous in organic chemistry, they are typically not associated with chirality and stereoisomerism. Due to the planarity and symmetry of simple arenes, methods to assemble aromatic rings are not routinely considered for the stereoselective synthesis of chiral compounds. The aim of this tutorial review is to contrast this common perception with the counterintuitive circumstance that stereoselective arene formation offers a means to stereoselectively prepare an exceptional range of chiral aromatic structures. The versatility of these methods across various types of molecular scaffolds allows to control stereocentre configuration, helical chiral compounds, the configuration of rotationally restricted stereogenic axes, planar chiral molecules or curved polyaromatic systems. Furthermore, stereoselective arene formation holds great promise for the selective construction of extended but structurally well-defined chiral structures.

Graphical abstract: Stereoselective arene formation

Article information

Article type
Tutorial Review
Submitted
15 Dec 2017
First published
22 Mar 2018

Chem. Soc. Rev., 2018,47, 3804-3815

Stereoselective arene formation

A. Link and C. Sparr, Chem. Soc. Rev., 2018, 47, 3804 DOI: 10.1039/C7CS00875A

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