title: Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles.
abstract: Heavily substituted cyclopropane esters were prepared in high yields, complete diastereoselection and high (up to 96%) enantioselectivity. The reaction described herein entailed reacting 4-nitro-5-styrylisoxazoles, a class of cinnamate synthetic equivalent, with 2-bromomalonate esters under the catalysis of 5 mol% of a Cincona derived phase-transfer catalyst. The reaction allowed multi-gram preparation of 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.
authors.forename: Claudia
authors.initials: C
authors.lastname: Del Fiandra
authors.forename: Linda
authors.initials: L
authors.lastname: Piras
authors.forename: Francesco
authors.initials: F
authors.lastname: Fini
authors.forename: Paolo
authors.initials: P
authors.lastname: Disetti
authors.forename: Maria
authors.initials: M
authors.lastname: Moccia
authors.forename: Mauro F A
authors.initials: MF
authors.lastname: Adamo
mesh_terms: D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D004952:Esters; D010080:Oxazoles; C030797:cyclopropane