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Issue 11, 2018
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Stereoselective arene formation

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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

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Publication details

The article was received on 15 Dec 2017 and first published on 22 Mar 2018


Article type: Tutorial Review
DOI: 10.1039/C7CS00875A
Citation: Chem. Soc. Rev., 2018,47, 3804-3815
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    Stereoselective arene formation

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

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