Asymmetric Synthesis of β-Ketoamides by Sulfonium Rearrangement.
1,3-dicarbonyl
Enantioselective synthesis
amide activation
sulfonium-rearrangement
β-ketoamide
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
23 Oct 2024
23 Oct 2024
Historique:
revised:
15
10
2024
received:
19
09
2024
accepted:
16
10
2024
medline:
23
10
2024
pubmed:
23
10
2024
entrez:
23
10
2024
Statut:
aheadofprint
Résumé
The synthesis of enantioenriched α-substituted 1,3‑dicarbonyls remains a contemporary challenge in synthesis due to their tendency to undergo racemization via keto-enol tautomerization. Herein, we report a method to access enantioenriched β-ketoamides by a chiral sulfinimine-mediated [3,3]-sigmatropic sulfonium rearrangement. The transformation displays good chirality transfer, as well as excellent chemoselectivity and functional group tolerance. Diastereoselective reduction of the ketone moiety, also achievable in one-pot fashion, affords enantioenriched β‑hydroxyamides.
Identifiants
pubmed: 39440410
doi: 10.1002/anie.202418070
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202418070Informations de copyright
© 2024 Wiley‐VCH GmbH.