A Boron Scan of Ethyl Acetoacetate Leads to Versatile Building Blocks.
acetoacetate
acylboronate
homologation
pyrazolone
regioselectivity
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:
26 Jan 2024
26 Jan 2024
Historique:
revised:
24
01
2024
received:
22
12
2023
accepted:
25
01
2024
medline:
26
1
2024
pubmed:
26
1
2024
entrez:
26
1
2024
Statut:
aheadofprint
Résumé
Discovered in the 19th century, ethyl acetoacetate has been central to the development of organic chemistry, including its pedagogy and applications. In this study, we present borylated derivatives of this venerable molecule. A boron handle has been installed at either [[EQUATION]]- or [[EQUATION]]-position of acetoacetate by homologation of acyl-MIDA (N-methyliminodiacetic acid) boronates with diazoacetates. Either alkyl or boryl groups were found to migrate with regiochemistry being a function of the steric bulk of the diazo species. Boryl [[EQUATION]]-ketoesters can be further modified into borylated pyrazolones and oximes, thereby expanding the synthetic toolkit and offering opportunities for additional modifications.
Identifiants
pubmed: 38277239
doi: 10.1002/anie.202319842
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202319842Informations de copyright
© 2024 Wiley-VCH GmbH.