Journal article
1,2-redox transpositions of tertiary amides
- Abstract:
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Reactions capable of transposing the oxidation levels of adjacent carbon atoms enable rapid and fundamental alteration of a molecule’s reactivity. Herein, we report the 1,2-transposition of the carbon atom oxidation level in cyclic and acyclic tertiary amides, resulting in the one-pot synthesis of 1,2- and 1,3-oxygenated tertiary amines. This oxidation level transfer was facilitated by the careful orchestration of an iridium-catalyzed reduction with the functionalization of transiently formed enamine intermediates. A novel 1,2-carbonyl transposition is described, and the breadth of this redox transposition strategy has been further explored by the development of aminoalcohol and enaminone syntheses. The diverse β-functionalized amine products were shown to be multifaceted and valuable synthetic intermediates, accessing challenging biologically relevant motifs.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 2.3MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.3c08466
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 145
- Issue:
- 40
- Pages:
- 21745-21751
- Publication date:
- 2023-09-27
- Acceptance date:
- 2023-09-27
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Pmid:
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37756523
- Language:
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English
- Keywords:
- Pubs id:
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1537256
- Local pid:
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pubs:1537256
- Deposit date:
-
2023-10-03
Terms of use
- Copyright holder:
- Shennan et al.
- Copyright date:
- 2023
- Rights statement:
- Copyright © 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.
- Notes:
- This research was funded in part by the EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine (EP/L015838/1). For the purpose of Open Access, the author has applied a CC BY public copyright licence to any Author Accepted Manuscript (AAM) version arising from this submission.
- Licence:
- CC Attribution (CC BY)
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