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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Bibliographic Details
Published inOrganic letters Vol. 12; no. 16; pp. 3598 - 3601
Main Authors Dabrowski, Jennifer A, Moebius, David C, Wommack, Andrew J, Kornahrens, Anne F, Kingsbury, Jason S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2010
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Diazomethane - analogs & derivatives
Diazomethane - chemistry
Ligands
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Trimethylsilyl Compounds - chemistry
REARRANGEMENT
ORGANIC-SYNTHESIS
KETONES
DIAZOMETHANE
ENANTIOSELECTIVE SYNTHESIS
SYNTHETIC REACTIONS
ASYMMETRIC EPOXIDATION
ALDEHYDES
HOMOLOGATION
CYCLOPENTANONES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol101136a