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A Chiral Interlocking Auxiliary Strategy for the Synthesis of Mechanically Planar Chiral Rotaxanes

preprint
revised on 12.03.2021, 14:45 and posted on 15.03.2021, 05:27 by Alberto de Juan, David Lozano, Andrew Heard, Michael Jinks, Jorge Meijide Suarez, Stephen Goldup
We have serendipitously discovered a combination of reaction partners that function as a “chiral interlocking auxiliary” to both orientate a macrocycle and, effectively, load it onto a new axle. We demonstrate the potential of this finding through the synthesis of a number of targets in high enantiopurity, without separation of stereoisomers, including examples whose axles lack any functional groups that would allow their direct synthesis by other means, so called “impossible” rotaxanes. Intriguingly, by varying the order of bond forming steps, we can effectively choose which end of an axle the macrocycle is loaded onto, allowing the synthesis of both hands of a single target using the same reactions and building blocks.

Funding

European Research Council (consolidator grant agreement no. 724987)

Leverhulme Trust (ORPG-2733)

Royal Society Wolfson Research Fellowship

Royal Society Newton International Fellowship

History

Email Address of Submitting Author

a.w.heard@soton.ac.uk

Institution

University of Southampton

Country

United Kingdom

ORCID For Submitting Author

0000-0002-6815-4618

Declaration of Conflict of Interest

No competing interests

Version Notes

Version_2_12032021

Exports