Stereoselective synthesis of mechanically planar chiral rotaxanes
Stereoselective synthesis of mechanically planar chiral rotaxanes
Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98: 2 d.r. using a readily available α amino acid‐derived azide. Symmetrisation of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.
14806-14810
Jinks, Michael
c8ce33cc-8ead-4763-b294-ae94ce0475d0
de Juan, Alberto
9b813dc1-b978-487d-82bf-d4bf5cafeb5d
Denis, Mathieu
b9a881a7-be8b-4dce-baee-cacc5fd9f277
Fletcher, Catherine
eb92b1b1-c153-4569-9929-fc6b395a9395
Galli, Marzia
c381f6fc-0d1a-4b01-a11a-2e6811dc1a3d
Jamieson, Ellen
49359222-1cf2-47af-98e5-d34f0c0c0933
Modicom, Florian
11482c31-fac9-4bb4-acdd-b79fbb2ae62b
Zhang, Zhihui
1cf08b0d-da64-4f84-a9dc-e70227af68a5
Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937
5 November 2018
Jinks, Michael
c8ce33cc-8ead-4763-b294-ae94ce0475d0
de Juan, Alberto
9b813dc1-b978-487d-82bf-d4bf5cafeb5d
Denis, Mathieu
b9a881a7-be8b-4dce-baee-cacc5fd9f277
Fletcher, Catherine
eb92b1b1-c153-4569-9929-fc6b395a9395
Galli, Marzia
c381f6fc-0d1a-4b01-a11a-2e6811dc1a3d
Jamieson, Ellen
49359222-1cf2-47af-98e5-d34f0c0c0933
Modicom, Florian
11482c31-fac9-4bb4-acdd-b79fbb2ae62b
Zhang, Zhihui
1cf08b0d-da64-4f84-a9dc-e70227af68a5
Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937
Jinks, Michael, de Juan, Alberto, Denis, Mathieu, Fletcher, Catherine, Galli, Marzia, Jamieson, Ellen, Modicom, Florian, Zhang, Zhihui and Goldup, Stephen
(2018)
Stereoselective synthesis of mechanically planar chiral rotaxanes.
Angewandte Chemie International Edition, 57 (45), .
(doi:10.1002/anie.201808990).
Abstract
Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98: 2 d.r. using a readily available α amino acid‐derived azide. Symmetrisation of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.
Text
MS Jinks Diastereoselectivity Angew
- Accepted Manuscript
More information
Accepted/In Press date: 24 September 2018
e-pub ahead of print date: 25 September 2018
Published date: 5 November 2018
Identifiers
Local EPrints ID: 423566
URI: http://eprints.soton.ac.uk/id/eprint/423566
ISSN: 1433-7851
PURE UUID: 99702877-676b-46e2-ad1c-2ae3c4169067
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Date deposited: 26 Sep 2018 16:30
Last modified: 16 Mar 2024 07:06
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Contributors
Author:
Michael Jinks
Author:
Alberto de Juan
Author:
Mathieu Denis
Author:
Catherine Fletcher
Author:
Marzia Galli
Author:
Ellen Jamieson
Author:
Florian Modicom
Author:
Zhihui Zhang
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