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Catalytic and Regioselective Ring Expansion of Arylcyclobutanones with Trimethylsilyldiazomethane. Ligand-Dependent Entry to beta-Ketosilane or Enolsilane Adducts

  作者 DABROWSKI JENNIFER A; MOEBIUS DAVID C; WOMMACK ANDREW J; KORNAHRENS ANNE F; KINGSBURY JASON S  
  选自 期刊  Organic Letters;  卷期  2010年12-16;  页码  3598-3601  
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[摘要]Divergent reactivity is uncovered in the homologation of arylcyclobutanones with trimethylsilyldiazomethane. With Sc(OTf)(3) as catalyst, enolsilanes are obtained with a high preference for methylene migration. By contrast, Sc(hfac)(3) gives beta-ketosilanes with both regio- and diastereocontrol. Each adduct affords the cyclopentanone upon hydrolysis.

 
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