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Intermolecular Radical Reaction of O,Se-Acetals Generated via Seleno-Pummerer Rearrangement

  作者 URABE DAISUKE; YAMAGUCHI HIROKI; SOMEYA AYUMI; INOUE MASAYUKI  
  选自 期刊  Organic Letters;  卷期  2012年14-15;  页码  3842-3845  
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[摘要]A new general protocol for the synthesis of O,Se-acetals using the seleno-Pummerer reaction has been developed, and their radical-based two-and three-component coupling reactions were studied. The three-component coupling employed the O,Se-acetal, cyclopentenone, and an allylstannane derivative, and enabled stereoselective installations of alpha-acyloxy alkyl and functionalized allyl groups to generate the 2,3-trans-disubstituted cyclopentanone in a single operation. The obtained highly functionalized structure was used as an intermediate for facile assembly of the zedoarondiol carboskeleton.

 
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