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

Mandrelli, Francesca; Blond, Aurélie; James, Thomas; Kim, Hyejin; List, Benjamin

doi:10.1002/anie.201905623

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

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Mandrelli, Francesca
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Blond, Aurélie
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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James, Thomas
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Kim, Hyejin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.

Cite as: https://hdl.handle.net/21.11116/0000-0004-6598-F

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.