title: Catalytic and regioselective ring expansion of arylcyclobutanones with trimethylsilyldiazomethane. Ligand-dependent entry to beta-ketosilane or enolsilane adducts.
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.
authors.affiliation: Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Dabrowski
authors.forename: David C
authors.initials: DC
authors.lastname: Moebius
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Wommack
authors.forename: Anne F
authors.initials: AF
authors.lastname: Kornahrens
authors.forename: Jason S
authors.initials: JS
authors.lastname: Kingsbury
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D003517:Cyclopentanes; D008024:Ligands; D014297:Trimethylsilyl Compounds; C007201:cyclopentanone; D003978:Diazomethane; C060070:trimethylsilyldiazomethane