title: Stereoselective synthesis of highly functionalized nitrocyclopropanes via organocatalyic conjugate addition to nitroalkenes.
abstract: A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported. The addition of dimethyl chloromalonate to a variety of nitroolefins catalyzed by tertiary amines leads to a Michael adduct which cyclizes to form the cyclopropane in the presence of DBU under carefully controlled reaction conditions with outstanding diastereoselectivity.
authors.affiliation: Centre for Synthesis and Chemical Biology and School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
authors.forename: Séamus H
authors.initials: SH
authors.lastname: McCooey
authors.forename: Thomas
authors.initials: T
authors.lastname: McCabe
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Connon
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003521:Cyclopropanes; D009574:Nitro Compounds