Journal article
Dynamic kinetic resolution allows control of remote stereochemistry in asymmetric hydrogen borrowing alkylation
- Abstract:
- A catalytic asymmetric method for the synthesis of γ-substituted ketones via hydrogen borrowing alkylation of both racemic linear precursors and 1,5-diols is described. The base mediated racemization of an intermediate cyclohexenone to facilitates a dynamic kinetic resolution, affording highly enantioenriched cyclohexanes in excellent yields, which could be further functionalized by removal of the Ph* group. DFT modelling revealed the mode of enantioinduction to be a stepwise process comprising of a hydride transfer and a coordination change to a π-allylic enolate complex with the iridium catalyst.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 5.0MB, Terms of use)
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(Preview, Supplementary materials, pdf, 4.0MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.202424959
Authors
+ Engineering and Physical Sciences Research Council
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- Funder identifier:
- https://ror.org/0439y7842
- Grant:
- EP/W02246X/1
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 64
- Issue:
- 13
- Article number:
- e202424959
- Publication date:
- 2025-02-27
- Acceptance date:
- 2025-02-05
- DOI:
- EISSN:
-
1521-3773
- ISSN:
-
1433-7851
- Language:
-
English
- Keywords:
- Pubs id:
-
2083913
- Local pid:
-
pubs:2083913
- Deposit date:
-
2025-02-05
Terms of use
- Copyright holder:
- Cheang 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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