title: Zn-Catalyzed Diastereo- and Enantioselective Cascade Reaction of 3-Isothiocyanato Oxindoles and 3-Nitroindoles: Stereocontrolled Syntheses of Polycyclic Spirooxindoles.
abstract: A catalytic asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles and 3-nitroindoles has been disclosed with a chiral Zn(OTf)2/diphenylamine-linked bis(oxazoline) complex as the catalyst. A range of enantioenriched polycyclic spirooxindole derivatives containing three contiguous stereocenters were efficiently constructed in quantitative yields with excellent diastereo- and enantioselectivities. Importantly, the metal catalytic strategy in this work is significantly superior to the previous organocatalytic method in the diastereo- and enantioselectivities for almost all of the examined cases.
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.|University of Chinese Academy of Sciences , Beijing 100049, China.
authors.forename: Jian-Qiang
authors.initials: JQ
authors.lastname: Zhao
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences , Chengdu 610041, China.
authors.forename: Zhi-Jun
authors.initials: ZJ
authors.lastname: Wu
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
authors.forename: Ming-Qiang
authors.initials: MQ
authors.lastname: Zhou
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
authors.forename: Xiao-Ying
authors.initials: XY
authors.lastname: Xu
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004159:Diphenylamine; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D007211:Indoles; D017879:Isothiocyanates; D009574:Nitro Compounds; D000078183:Oxindoles; D011083:Polycyclic Compounds; D013141:Spiro Compounds; C022960:2-oxindole; D004159:Diphenylamine; D015032:Zinc