title: Photochemically-induced C-C bond formation between tertiary amines and nitrones.
abstract: Photoexcited nitrones serve as excellent electron acceptors as well as radical acceptors in the presence of tertiary amines to give β-amino hydroxylamines via photochemically-induced direct sp(3) C-H functionalization of the tertiary amines. The combined use of an organophotosensitizer and photoirradiation was highly effective in accelerating addition reactions. Several nitrones and tertiary amines were successfully utilized to give β-amino hydroxylamines in good yield. Highly regioselective generation of primary α-aminoalkyl radicals based on Lewis's stereoelectronic rule and diastereoselective addition reactions of primary α-aminoalkyl radicals with nitrones were successfully achieved. Furthermore, a highly diastereoselective reaction of an α-aminoalkyl radical with a chiral (E)-geometry-fixed α-alkoxycarbonylnitrone was performed.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan. itok@pharm.kitasato-u.ac.jp.
authors.forename: Kennosuke
authors.initials: K
authors.lastname: Itoh
authors.forename: Ryo
authors.initials: R
authors.lastname: Kato
authors.forename: Daito
authors.initials: D
authors.lastname: Kinugawa
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kamiya
authors.forename: Ryuki
authors.initials: R
authors.lastname: Kudo
authors.forename: Masayuki
authors.initials: M
authors.lastname: Hasegawa
authors.forename: Hideaki
authors.initials: H
authors.lastname: Fujii
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Suga
mesh_terms: D000588:Amines / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D055668:Photochemical Processes; D017319:Photosensitizing Agents; D066244:Proton Magnetic Resonance Spectroscopy; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014466:Ultraviolet Rays
chemical_list: D000588:Amines; D009589:Nitrogen Oxides; D017319:Photosensitizing Agents; D012997:Solvents; C015388:nitrones