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Remote Control of the C-3-C-4 Double-Bond Epoxidation of a Chiral 1,2-Dihydroquinoline: Application to the Synthesis of (-)-(R)-Sumanirole (PNU-95666E)

  作者 JEANGERARD LUDIVINE; MACE FREDERIC; ANH NGOC NGO; PAUVERT MICKAEL; DENTEL HELENE; EVAIN MICHEL; COLLET SYLVAIN; GUINGANT ANDRE  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2012年-22;  页码  4240-4248  
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[摘要]A twelve-step synthesis of ()-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1.

 
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