title: Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.
abstract: Rhodium-catalyzed reaction of vinyldiazoacetates with nitrones results in a formal [3+2]-cycloaddition to generate 2,5-dihydroisoxazoles with high levels of asymmetric induction. The cascade reaction begins with a vinylogous addition event, followed by an iminium addition ring-closure/hydride migration/alkene isomerization cascade. Dirhodium tetrakis(triarylcyclopropanecarboxylates) are the optimum catalysts for this process.
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Changming
authors.initials: C
authors.lastname: Qin
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
mesh_terms: D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D007555:Isoxazoles; D009589:Nitrogen Oxides; D014753:Vinyl Compounds; C015388:nitrones; D012238:Rhodium; C011566:vinyl acetate
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