title: Electrochemical intramolecular aminooxygenation of unactivated alkenes.
abstract: An electrochemical approach to the intramolecular aminooxygenation of unactivated alkenes has been developed. This process is based on the addition of nitrogen-centered radicals, generated through electrochemical oxidation, to alkenes followed by trapping of the cyclized radical intermediate with 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO). Difunctionalization of a variety of alkenes with easily available carbamates/amides and TEMPO affords aminooxygenation products in high yields and with excellent trans selectivity for cyclic systems (d.r. up to>20:1). The approach provides a much-needed complementary route to existing cis-selective methods.
authors.affiliation: The Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (China) http://chem.xmu.edu.cn/kydw_ktz/hcxu/index.html.
authors.forename: Fan
authors.initials: F
authors.lastname: Xu
authors.forename: Lin
authors.initials: L
authors.lastname: Zhu
authors.forename: Shaobin
authors.initials: S
authors.lastname: Zhu
authors.forename: Xiaomei
authors.initials: X
authors.lastname: Yan
authors.forename: Hai-Chao
authors.initials: HC
authors.lastname: Xu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003500:Cyclization; D055664:Electrochemical Techniques; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D000577:Amides; D000588:Amines; D002219:Carbamates; D003497:Cyclic N-Oxides; D009584:Nitrogen; C003959:TEMPO
keywords: amino alcohols; aminooxygenation; cyclization; electrochemical oxidation; radicals