title: Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions.
abstract: A silica-supported dirhodium(II) tetraprolinate catalyst was synthesized in four steps from l-proline and used in a range of enantioselective transformations of donor/acceptor carbenoids. These include cyclopropenation, cyclopropanation, tandem ylide formation/[2,3] sigmatropic rearrangement, and a variety of combined C-H functionalization/Cope rearrangement reactions. The products of these transformations were obtained in yields and levels of enantioselectivity comparable to those obtained with its homogeneous counterpart, Rh2(S-DOSP)4. The silica-supported Rh2(S-DOSP)4 derivative was successfully recycled over five reactions.
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States , and School of Chemical & Biomolecular Engineering, Georgia Institute of Technology , 311 Ferst Drive, Atlanta, Georgia 30322, United States.
authors.forename: Kathryn M
authors.initials: KM
authors.lastname: Chepiga
authors.forename: Yan
authors.initials: Y
authors.lastname: Feng
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Brunelli
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Jones
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
mesh_terms: D002384:Catalysis; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009942:Organometallic Compounds; C030011:carbene; D012822:Silicon Dioxide; D011392:Proline; D012238:Rhodium; D008697:Methane