The synthesis of mechanically planar chiral rotaxanes and their application to enantioselective catalysis

Abstract

Mechanically interlocked molecules have been of interest to chemists since the 1960s. Recent synthetic advances have made the investigation of the mechanical bond more accessible, with most applications of interlocked molecules in molecular machines. The field of interlocked molecules was acknowledged by the Nobel committee in 2016, with the prestigeous prize being awarded to Sir J. Fraser Stoddart, Jean-Pierre Sauvage and Ben Feringa for their contribution to “the design and synthesis of molecular machines”. This thesis discusses mechanical planar chirality, the challenging synthesis of interlocked molecules displaying this type of chirality, and the first application of this type of chirality in enantioselective catalysis. Finally this thesis presents a new, general approach to the synthesis of interlocked molecules displaying this type of chirality, allowing unprecedented access to enantiopure rotaxanes and a library of ligands for catalysis by application of this methodology.

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Identifiers

ORCID for Stephen Goldup: orcid.org/0000-0003-3781-0464

ORCID for Ramon Rios Torres: orcid.org/0000-0002-3843-8521

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