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A Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis

preprint
revised on 23.08.2019 and posted on 23.08.2019 by Andrew Heard, Stephen Goldup

Rotaxanes are interlocked molecules in which a molecular ring is trapped on a dumbbell-shaped axle due to its inability to escape over the bulky end groups, resulting in a so-called mechanical bond. Interlocked molecules have mainly been studied as components of molecular machines, but the crowded, flexible environment created by threading one molecule through another, reminiscent of the active site of an enzyme, has also been explored in catalysis and sensing. However, so far the applications of one of the most intriguing properties of interlocked molecules, their ability to display stereogenic units that do not rely on the stereochemistry of their covalent subunits, termed "mechanical chirality", have yet to be properly explored and prototypical demonstration of the applications of mechanically chiral rotaxanes remain scarce. Here we describe a mechanically planar chiral rotaxane-based Au complex that mediates a cyclopropanation reaction with stereoselectivities that are comparable with conventional covalent catalyst reported for this reaction.

Funding

European Research Council (Consolidator Grant Agreement no. 724987)

Leverhulme Trust (ORPG-2733)

Royal Society (Wolfson Research Fellowship to SMG)

EPSRC (studentship to AWH)

History

Email Address of Submitting Author

s.goldup@soton.ac.uk

Institution

University of Southampton

Country

United Kingdom

ORCID For Submitting Author

0000-0003-3781-0464

Declaration of Conflict of Interest

no conflicts of interest

Exports