title: Copper Nitrate Mediated Regioselective [2+2+1] Cyclization of Alkynes with Alkenes: A Cascade Approach to Δ(2)-Isoxazolines.
abstract: An efficient method for the regioselective synthesis of pharmacologically relevant polysubstituted Δ(2)-isoxazolines is based on the copper-mediated direct transformation of simple terminal alkynes and alkenes. The overall process involves the formation of four chemical bonds with inexpensive and readily available copper nitrate trihydrate as a novel precursor of nitrile oxides. The reaction can be easily handled and proceeds under mild conditions.
authors.affiliation: School of Materials Science and Engineering, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444 (China) http://www.xubin.shu.edu.cn.
authors.forename: Mingchun
authors.initials: M
authors.lastname: Gao
authors.affiliation: School of Materials Science and Engineering, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444 (China) http://www.xubin.shu.edu.cn.
authors.forename: Yingying
authors.initials: Y
authors.lastname: Li
authors.affiliation: School of Materials Science and Engineering, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444 (China) http://www.xubin.shu.edu.cn.
authors.forename: Yuansheng
authors.initials: Y
authors.lastname: Gan
authors.affiliation: School of Materials Science and Engineering, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444 (China) http://www.xubin.shu.edu.cn. xubin@shu.edu.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China). xubin@shu.edu.cn.|Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062 (China). xubin@shu.edu.cn.
authors.forename: Bin
authors.initials: B
authors.lastname: Xu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009566:Nitrates / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D007555:Isoxazoles; D009566:Nitrates; D009570:Nitriles; D010087:Oxides; D003300:Copper; C516433:copper(II) nitrate
keywords: alkenes; alkynes; cascade reactions; copper; isoxazolines