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Ligand-Controlled Selectivity in the Desymmetrization of meso Cyclopenten-1,4-diols via Rhodium(I)-Catalyzed Addition of Arylboronic Acids

  作者 MENARD FREDERIC; PEREZ DAVID; ROMAN DANIELA SUSTAC; CHAPMAN TIMOTHY M; LAUTENS MARK  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-12;  页码  4056-4068  
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[摘要]A highly enantioselective & symmetrization of mesa cyclopent-2-ene-1,4-diethyl dicarbonates has been developed using a Rh-catalyzed asymmetric allylic substitution. Depending on the type of ligand used, each of two regioisomeric products can be obtained in good yield and excellent enantioselectivity. Under rhodium(I) catalysis, bisphosphinc P-Phos ligands form trans-1,2-arylcyclopentenols as the major product, whereas Segphos ligands lead predominantly to trans-1,4-arylcyclopentenols.

 
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