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Organic letters

Catalytic and regioselective ring expansion of arylcyclobutanones with trimethylsilyldiazomethane. Ligand-dependent entry to beta-ketosilane or enolsilane adducts.


PMID 20669953

Abstract

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.