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      Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.

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      Journal of the American Chemical Society

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          Abstract

          The enantioselective α-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

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          Author and article information

          Journal
          J. Am. Chem. Soc.
          Journal of the American Chemical Society
          1520-5126
          0002-7863
          Mar 30 2011
          : 133
          : 12
          Affiliations
          [1 ] Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
          Article
          NIHMS279525
          10.1021/ja2008906
          3082494
          21388207
          2745d452-6d0b-4f85-9f37-d86a04691f08
          History

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