title: Asymmetric Construction of Spirooxindoles by Organocatalytic Multicomponent Reactions Using Diazooxindoles.
abstract: The first highly diastereo- and enantioselective multicomponent reaction of diazooxindoles, nitrosoarenes, and nitroalkenes using a newly developed hydrogen-bond catalyst has been successfully developed for the efficient construction of a series of spirooxindole derivatives with excellent functional-group tolerance. Spirooxindoles are formed in excellent yields and stereoselectivities, and the method represents an unprecedented approach for trapping the active intermediate with a nitroalkene to form biologically important compounds having three contiguous stereogenic centers with excellent asymmetric induction.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Ming-Yue
authors.initials: MY
authors.lastname: Wu
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
authors.forename: Wei-Wei
authors.initials: WW
authors.lastname: He
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China). liuxy3@sustc.edu.cn.
authors.forename: Xin-Yuan
authors.initials: XY
authors.lastname: Liu
authors.affiliation: Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China). tanb@sustc.edu.cn.
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
mesh_terms: D002384:Catalysis; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D007211:Indoles; D013141:Spiro Compounds; D013890:Thiourea
keywords: diazo compounds; enantioselectivity; heterocycles; multicomponent reactions; organocatalysis