title: Formal substitution of bromocyclopropanes with nitrogen nucleophiles.
abstract: A highly chemo- and diastereoselective protocol toward amino-substituted donor-acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cyclopropylamine derivatives.
authors.affiliation: Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-75832, USA.
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Banning
authors.forename: Jacob
authors.initials: J
authors.lastname: Gentillon
authors.forename: Pavel G
authors.initials: PG
authors.lastname: Ryabchuk
authors.forename: Anthony R
authors.initials: AR
authors.lastname: Prosser
authors.forename: Andrew
authors.initials: A
authors.lastname: Rogers
authors.forename: Andrew
authors.initials: A
authors.lastname: Edwards
authors.forename: Andrew
authors.initials: A
authors.lastname: Holtzen
authors.forename: Ivan A
authors.initials: IA
authors.lastname: Babkov
authors.forename: Marina
authors.initials: M
authors.lastname: Rubina
authors.forename: Michael
authors.initials: M
authors.lastname: Rubin
mesh_terms: D000577:Amides / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001393:Azoles / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000577:Amides; D000814:Aniline Compounds; D001393:Azoles; D003521:Cyclopropanes; D013449:Sulfonamides; C067351:cyclopropylamine; C023650:aniline