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      Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters

      1 , 1 , 1

      Journal of the American Chemical Society

      American Chemical Society (ACS)

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          Abstract

          <p class="first" id="P1">Enantioconvergent arylation reactions of boronic acids and racemic β-stereogenic α-keto esters have been developed. The reactions are catalyzed by a chiral (diene)Rh(I) complex and provide a wide array of β-stereogenic tertiary aryl glycolate derivatives with high levels of diastereo- and enantioselectivity. Racemization studies employing a series of sterically differentiated tertiary amines suggest that the steric nature of the amine base additive exerts a significant influence on the rate of substrate racemization. </p><p id="P2"> <div class="figure-container so-text-align-c"> <img alt="" class="figure" src="/document_file/5e355792-a159-4340-8fd7-e879f9765c66/PubMedCentral/image/nihms853548u1.jpg"/> </div> </p>

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          Author and article information

          Journal
          Journal of the American Chemical Society
          J. Am. Chem. Soc.
          American Chemical Society (ACS)
          0002-7863
          1520-5126
          March 07 2017
          March 15 2017
          March 02 2017
          March 15 2017
          : 139
          : 10
          : 3911-3916
          Affiliations
          [1 ]Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States
          Article
          10.1021/jacs.7b00943
          5352479
          28252953
          © 2017
          Product

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