Synthesis of a Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis

Steve Goldup reports on a planar chiral rotaxane ligand for enantioselective catalysis.

Rotaxanes are interlocked molecules in which a molecular ring is threaded onto a dumbbell-shaped axle which bears end groups too large to fit through the cavity of the ring. Professor Steve Goldup from the University of Southampton (UK) explained that rotaxanes are most famous as components of molecular machines, which function by exploiting the controlled movement of the ring along the axle. However, there is a growing interest in how the chemical properties of rotaxanes, and other interlocked molecules, can be exploited to solve chemical problems, for example in catalysis, sensing, materials science and medicinal chemistry. As part of a research project focused on investigating the unusual stereochemical properties of interlocked molecules, Professor Steve Goldup and postgraduate student Andrew Heard developed a rotaxane-based gold complex that carries out an enantioselective cyclopropanation reaction.

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