title: Enantioselective cyclopropanation of (Z)-3-substituted-2-(4-pyridyl)-acrylonitriles catalyzed by Cinchona ammonium salts.
abstract: Cyclopropane esters holding two quaternary centres were prepared in high yields, complete diastereoselection and up to 83% ee. The reaction described herein entailed reacting (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor, with 2-bromomalonate esters in the presence of Cinchona derived phase-transfer catalysts. The reaction allowed multi-gram preparation of the desired products.
authors.affiliation: Centre for Synthesis and Chemical Biology (CSCB), Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St Stephen's Green, Dublin 2, Ireland. madamo@rcsi.ie.
authors.forename: Claudia
authors.initials: C
authors.lastname: Del Fiandra
authors.forename: Maria
authors.initials: M
authors.lastname: Moccia
authors.forename: Mauro F A
authors.initials: MF
authors.lastname: Adamo
mesh_terms: D000181:Acrylonitrile / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D064751:Ammonium Compounds / Q000737:chemistry*; D002384:Catalysis; D002929:Cinchona / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004951:Esterification; D054879:Halogenation; D008314:Malonates / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D064751:Ammonium Compounds; D003521:Cyclopropanes; D008314:Malonates; C030797:cyclopropane; D000181:Acrylonitrile