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Deracemizing α‐Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis‐Silyl Ketene Acetals with Water or Methanol
Authors:Francesca Mandrelli  Aurlie Blond  Thomas James  Hyejin Kim  Benjamin List
Institution:Francesca Mandrelli,Aurélie Blond,Thomas James,Hyejin Kim,Benjamin List
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.
Keywords:bis-silyl ketene acetals  Brø  nsted acids  deracemization  deuteration  disulfonimide  protonation
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