de Juan, A, Lozano, D, Heard, AW et al. (4 more authors) (2021) A chiral interlocking auxiliary strategy for the synthesis of mechanically planar chiral rotaxanes. Nature Chemistry, 14. pp. 179-187. ISSN 1755-4330
Abstract
Rotaxanes can display molecular chirality solely due to the mechanical bond between the axle and encircling macrocycle without the presence of covalent stereogenic units. However, the synthesis of such molecules remains challenging. We have 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. Here we use these substrates to demonstrate the potential of a chiral interlocking auxiliary strategy for the synthesis of mechanically planar chiral rotaxanes by producing a range of examples with high enantiopurity (93–99% e.e.), including so-called ‘impossible’ rotaxanes whose axles lack any functional groups that would allow their direct synthesis by other means. Intriguingly, by varying the order of bond-forming steps, we can effectively choose which end of an axle the macrocycle is loaded onto, enabling the synthesis of both hands of a single target using the same reactions and building blocks.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 05 Jan 2022 15:21 |
Last Modified: | 11 Feb 2022 13:21 |
Status: | Published |
Publisher: | Nature Research |
Identification Number: | 10.1038/s41557-021-00825-9 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:181829 |