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

Mandrelli, F., Blond, A., James, T., Kim, H., & List, B. (2019). Deracemizing α‐Branched Carboxylic Acids by Catalytic Asymmetric Protonation of bis‐Silyl Ketene Acetals with Water or Methanol. Angewandte Chemie International Edition, 58(33), 11479-11482. doi:10.1002/anie.201905623.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0004-6598-F Version Permalink: https://hdl.handle.net/21.11116/0000-0008-54CA-6
Genre: Journal Article

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Mandrelli, Blond, James, Kim, List 2019.pdf (Postprint), 2MB
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 Creators:
Mandrelli, Francesca1, Author           
Blond, Aurélie1, Author           
James, Thomas1, Author           
Kim, Hyejin1, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: bis-silyl ketene acetals; Brønsted acids; deracemization; deuteration; disulfonimide; protonation
 Abstract: 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.

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Language(s): eng - English
 Dates: 2019-05-062019-05-272019-05-272019-08-12
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201905623
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 58 (33) Sequence Number: - Start / End Page: 11479 - 11482 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851