Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol.
Brønsted acids
bis-silyl ketene acetals
deracemization
deuteration
disulfonimide
protonation
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:
12 08 2019
12 08 2019
Historique:
received:
06
05
2019
pubmed:
28
5
2019
medline:
28
5
2019
entrez:
28
5
2019
Statut:
ppublish
Résumé
We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.
Identifiants
pubmed: 31131975
doi: 10.1002/anie.201905623
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
11479-11482Subventions
Organisme : European Research Council
ID : Advanced Grant "C-H Acids for Organic Synthesis, CHAOS
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.