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

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

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 β-ketosilanes with both regio- and diastereocontrol. Each addu...

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Veröffentlicht in:Organic letters 2010-08, Vol.12 (16), p.3598-3601
Hauptverfasser: Dabrowski, Jennifer A, Moebius, David C, Wommack, Andrew J, Kornahrens, Anne F, Kingsbury, Jason S
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Combinatorial Chemistry Techniques
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Diazomethane - analogs & derivatives
Diazomethane - chemistry
Ligands
Molecular Structure
Stereoisomerism
Trimethylsilyl Compounds - chemistry
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Zusammenfassung: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 β-ketosilanes with both regio- and diastereocontrol. Each adduct affords the cyclopentanone upon hydrolysis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101136a