Journal article
Cobalt‐catalyzed enantio‐ and regioselective C(sp3)−H alkenylation of thioamides
- Abstract:
- An enantioselective cobalt-catalyzed C(sp3)−H alkenylation of thioamides with but-2-ynoate ester coupling partners employing thioamide directing groups is presented. The method is operationally simple and requires only mild reaction conditions, while providing alkenylated products as single regioisomers in excellent yields (up to 85 %) and high enantiomeric excess [up to 91 : 9 enantiomeric ratio (er), or up to >99 : 1 er after a single recrystallization]. Diverse downstream derivatizations of the products are demonstrated, delivering a range of enantioenriched constructs. Extensive computational studies using density functional theory provide insight into the detailed reaction mechanism, origin of enantiocontrol, and the unusual regioselectivity of the alkenylation reaction.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 7.1MB, Terms of use)
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- Publisher copy:
- 10.1002/ange.202316021
Authors
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie More from this journal
- Volume:
- 136
- Issue:
- 13
- Article number:
- e202316021
- Publication date:
- 2024-02-23
- Acceptance date:
- 2023-12-20
- DOI:
- EISSN:
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1521-3757
- ISSN:
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0044-8249
- Language:
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English
- Keywords:
- Pubs id:
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1686553
- Local pid:
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pubs:1686553
- Deposit date:
-
2024-03-10
Terms of use
- Copyright holder:
- Staronova et al
- Copyright date:
- 2023
- Rights statement:
- © 2023 The Authors. Angewandte Chemie 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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