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Catalytic Parallel Kinetic Resolution under Homogeneous Conditions

  作者 DUFFEY TRISHA A; MACKAY JAMES A; VEDEJS EDWIN  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-14;  页码  4674-4685  
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[摘要]Two complementary chiral catalysts, the phosphine 8d and the DMAP-derived ent-23b, are used simultaneously to selectively activate a mixture of two different achiral anhydrides as acyl donors under homogeneous conditions. The resulting activated intermediates 25 and 26 react with the racemic benzylic alcohol 5 to form enantioenriched esters (R)-24 and (S)-17 by fully catalytic parallel kinetic resolution (PKR). The aroyl ester (R)-24 is obtained with near-ideal enantioselectivity for the PKR process, but (S)-17 is contaminated by ca. 8% of the minor enantiomer (R)-17 resulting from a second pathway via formation of mixed anhydride 27 and its activation by 8d.

 
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