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Volume 556 Issue 7702, 26 April 2018

Molecular control

Carbon atoms with four different carbon substituents — quaternary stereocentres — are key structural motifs in biologically active small organic molecules. These molecules can have distinct mirror images and synthesizing only the correct configuration can be a challenge. In this issue Eric Jacobsen and his colleagues reveal how they selectively produced quaternary stereocentres from a racemic mixture using a reaction mechanism that usually cannot be controlled. The unimolecular nucleophilic substitution (SN1) reaction is ubiquitous in organic chemistry textbooks. It allows an incoming nucleophile to replace one of the existing substituents on a carbon atom via a planar cationic intermediate (featured on the cover). But the nature of the mechanism means that the nucleophile can approach the reactive carbon atom from either face meaning that it is usually impossible to add the incoming group selectively. By using a chiral hydrogen-bonding catalyst and a Lewis acid Jacobsen and his team have broken that rule allowing the SN1 reaction to progress in a stereocontrolled fashion.

Cover image: Ella Maru Studio Inc.

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