title: Bicyclic pyrazolidinone derivatives from diastereoselective catalytic [3 + 3]-cycloaddition reactions of enoldiazoacetates with azomethine imines.
abstract: A highly regio- and diastereoselective synthesis of bicyclic pyrazolidinone derivatives by rhodium(II) acetate catalyzed [3 + 3]-annulation with enoldiazoacetates and azomethine imines has been achieved in high yield. A vinylogous reaction of the metal enol carbene with the azomethine imine initiates [3 + 3]-cycloaddition, whereas reaction at the carbene center effects N-N-cleavage of the azomethine imine.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Qian
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Zavalij
authors.forename: Wenhao
authors.initials: W
authors.lastname: Hu
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D007097:Imines / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007097:Imines; D011720:Pyrazoles; D013882:Thiosemicarbazones; C512188:azomethine; C030011:carbene; D012238:Rhodium; D008697:Methane