A Chiral Macrocycle for the Synthesis of Both Mechanically Planar Chiral Rotaxanes and Catenanes in Excellent Enantiopurity

28 September 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Active-template auxiliary methodologies have previously been developed for the stereoselective synthesis of chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit. To date however, the covalent auxiliary has been included in the half-axle components (rotaxanes) or pre-macrocycle components (catenanes), and thus mechanically chiral rotaxane and catenane syntheses rely on different chiral components. Here we present a single, simple amino acid-derived macrocycle that mediates the formation of both catenanes and rotaxanes in excellent stereoselectivity. We demonstrate the flexibility of our approach through the stereoselective synthesis of all three isomers of a co-conformationally mechanically planar chiral [3]rotaxane.

Keywords

Rotaxane
Catenane
Stereochemistry

Supplementary materials

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Supporting information
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Full characterisation and supplementary discussion
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Cif for 1e
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Crystallographic data
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Cif for 4a
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Crystallographic data
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Cif for 4b
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Crystallographic data
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Cif for 15
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Crystallographic data
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Cif for S20
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Crystallographic data
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