title: Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions.
abstract: The reaction between 3-methyl-4-nitro-5-styrylisoxazoles and ethyl isocyanoacetate proceeded under phase transfer catalysis to give enantioenriched monoadducts in high enantiomeric excess (up to 99% ee). The resulting adducts were subsequently cyclised to give 2,3-dihydropyrroles and substituted pyrrolidines in identical high ees and as a single diastereoisomer.
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: Paolo
authors.initials: P
authors.lastname: Disetti
authors.affiliation: National Research Council-Institute of Crystallography, Via G. Amendola 122/O, 70126 Bari, Italy.
authors.forename: Maria
authors.initials: M
authors.lastname: Moccia
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: Diana
authors.initials: D
authors.lastname: Salazar Illera
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: Surisetti
authors.initials: S
authors.lastname: Suresh
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: Mauro F A
authors.initials: MF
authors.lastname: Adamo
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D007555:Isoxazoles; D009570:Nitriles; D009574:Nitro Compounds; D011758:Pyrroles; D011759:Pyrrolidines; C013231:pyrroline