title: Halonium-initiated C-O bond formation via umpolung of α-carbon to the carbonyl: efficient access to 5-amino-3(2H)-furanones.
abstract: Highly efficient C-O bond formation has been developed via carboxylic acid catalyzed reaction of 1-acetylcyclopropanecarboxamides with N-halosuccinimide (NXS), which provides strategically novel and atom-economic access to biologically important 5-amino-3(2H)-furanones. The mechanism of halonium-initiated tandem oxa-cyclization and ring opening of cyclopropane was proposed. A variety of nucleophiles were found to open the cyclopropane.
authors.affiliation: Department of Chemistry, Northeast Normal University, Changchun 130024, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Wei
authors.forename: Shaoxia
authors.initials: S
authors.lastname: Lin
authors.forename: Hongxun
authors.initials: H
authors.lastname: Xue
authors.forename: Fushun
authors.initials: F
authors.lastname: Liang
authors.forename: Baozhong
authors.initials: B
authors.lastname: Zhao
mesh_terms: D000586:Amination; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D005663:Furans; D007477:Ions; D009861:Onium Compounds; D002244:Carbon; C039281:furan