Journal article
Asymmetric hydride shift reactions catalysed by chiral aluminium complexes
- Abstract:
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An asymmetric intramolecular hydride shift reaction has been developed that is catalysed by Al Lewis acids in conjunction with a chiral BINOL-derived ligand. Racemic THP substrates are transformed into cyclohexene products via a prochiral intermediate ring opened enone; which then undergoes a key 1,5-hydride shift reaction. This reaction is operationally simple, works well on a gram scale, and the desired products are formed with very high enantioselectivity (up to >98:2 e.r.). Importantly, the cyclohexene products contain functionality that can be easily derivatized and this is exemplified in the paper. Finally a model is presented for the enantioselective hydride shift that is based on previous DFT studies.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Supplementary materials, pdf, 2.0MB, Terms of use)
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(Preview, Version of record, pdf, 1.3MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.202521374
Authors
- Funder identifier:
- https://ror.org/0439y7842
- Grant:
- EP/W02246X/1
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 65
- Issue:
- 5
- Article number:
- e21374
- Publication date:
- 2025-12-18
- Acceptance date:
- 2025-12-05
- DOI:
- EISSN:
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1521-3773
- ISSN:
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1433-7851
- Language:
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English
- Keywords:
- Pubs id:
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2345749
- Local pid:
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pubs:2345749
- Deposit date:
-
2025-12-05
- ARK identifier:
Terms of use
- Copyright holder:
- Amer et al.
- Copyright date:
- 2025
- Rights statement:
- © 2025 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Licence:
- CC Attribution (CC BY)
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