title: Functionalized 4-carboxy- and 4-keto-2,3-dihydropyrroles via Ni(II)-catalyzed nucleophilic amine ring-opening cyclizations of cyclopropanes.
abstract: A general synthetic approach to vinylogous 4-carboxy- and 4-keto-2,3-dihydropyrroles is reported using Ni(ClO4)2·6H2O as a Lewis acid catalyst for nucleophilic amine ring-opening cyclizations of donor-acceptor (D-A) cyclopropanes. This methodology provided good to excellent yields of functionalized 2,3-dihydropyrroles under milder reaction conditions than previously reported and is amenable to a variety of D-A cyclopropanes and primary amines.
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.
authors.forename: M Cynthia
authors.initials: MC
authors.lastname: Martin
authors.forename: Dadasaheb V
authors.initials: DV
authors.lastname: Patil
authors.forename: Stefan
authors.initials: S
authors.lastname: France
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000588:Amines; D003521:Cyclopropanes; D058116:Lewis Acids; D011758:Pyrroles; D009532:Nickel