title: Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates.
abstract: Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Xinfang
authors.initials: X
authors.lastname: Xu
authors.forename: Dmitry
authors.initials: D
authors.lastname: Shabashov
authors.forename: Peter Y
authors.initials: PY
authors.lastname: Zavalij
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000586:Amination; D001391:Azo Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*
chemical_list: D000080:Acetals; D001391:Azo Compounds; D002264:Carboxylic Acids; D005663:Furans; D009570:Nitriles; D010087:Oxides; C039281:furan