Deracemizing α‐Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis‐Silyl Ketene Acetals with Water or Methanol

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 o...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-08, Vol.58 (33), p.11479-11482
Main Authors: Mandrelli, Francesca, Blond, Aurélie, James, Thomas, Kim, Hyejin, List, Benjamin
Format: Article
Language:English
Subjects:
Acetals
Acids
bis-silyl ketene acetals
Brønsted acids
Carboxylic acids
Catalysis
deracemization
deuteration
disulfonimide
Enantiomers
Ibuprofen
Inflammation
Protonation
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Summary: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. Highly enantioselective catalytic protonation of bis‐silyl ketene acetals 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201905623