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

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          Abstract

          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.

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          Journal
          7503056
          4435
          J Am Chem Soc
          J. Am. Chem. Soc.
          Journal of the American Chemical Society
          0002-7863
          1520-5126
          22 February 2017
          02 March 2017
          15 March 2017
          15 March 2018
          : 139
          : 10
          : 3911-3916
          Affiliations
          Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290 United States
          Author notes
          Corresponding Author: jsj@ 123456unc.edu
          Article
          PMC5352479 PMC5352479 5352479 nihpa853548
          10.1021/jacs.7b00943
          5352479
          28252953
          9d553dc9-6f6f-407f-b34e-5ed1b04e8b6c
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