title: Efficient and regioselective 9-endo cyclization of α-carbamoyl radicals.
abstract: With the promotion of Lewis acid BF(3)•OEt(2), various N-(hex-5-enyl)-2-iodoalkanamides underwent efficient and regioselective 9-endo iodine-atom-transfer radical cyclization reactions at room temperature. The cyclized products were readily converted to the corresponding azonan-2-ones by reduction with Bu(3)SnH or to hexahydroindolizin-3(5H)-ones by treatment with aqueous Na(2)CO(3) in a one-pot, two-stage manner.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.
authors.forename: Liyan
authors.initials: L
authors.lastname: Song
authors.forename: Kun
authors.initials: K
authors.lastname: Liu
authors.forename: Chaozhong
authors.initials: C
authors.lastname: Li
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D007212:Indolizines / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D005609:Free Radicals; D007212:Indolizines; C035094:indolizine