title: Diastereo- and enantioselective conjugate addition of 3-substituted oxindoles to nitroolefins catalyzed by a chiral Ni(OAc)2-diamine complex under mild conditions.
abstract: A simple catalyst system assembled from an enantiomerically pure diamine ligand and Ni(OAc)(2) efficiently generates chiral metal enolates derived from 3-substituted oxindoles bearing an N-1 carbonyl group. The enolates smoothly undergo diastereo- and enantioselective conjugate addition to a wide range of nitroolefins under mild reaction conditions, furnishing 3,3-disubstituted oxindole products bearing two vicinal quaternary/tertiary stereocenters in 74-95% yields and 60:40 to 99:1 dr, 71-97% ee.
authors: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors: Yan-Yan
authors: YY
authors: Han
authors: Zhi-Jun
authors: ZJ
authors: Wu
authors: Wen-Bing
authors: WB
authors: Chen
authors: Xi-Lin
authors: XL
authors: Du
authors: Xiao-Mei
authors: XM
authors: Zhang
authors: Wei-Cheng
authors: WC
authors: Yuan
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007211:Indoles; D008024:Ligands; D009574:Nitro Compounds; D009942:Organometallic Compounds; D000078183:Oxindoles; C022960:2-oxindole; D009532:Nickel