title: Asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles and 3-nitroindoles with amino-thiocarbamate catalysts: enantioselective synthesis of polycyclic spirooxindoles.
abstract: An unprecedented organocatalytic asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles and 3-nitroindoles has been disclosed. A wide range of enantioenriched polycyclic spirooxindoles, containing three contiguous chiral centers with two of them having quaternary stereocenters, could be smoothly obtained with satisfactory results (up to 99% yield, >99:1 dr, and 96% ee). This method is very promising because the reaction is scalable, and the versatile transformations of the products into other spirocyclic oxindoles are also feasible.
authors: †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: Jian-Qiang
authors: JQ
authors: Zhao
authors: †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: Ming-Qiang
authors: MQ
authors: Zhou
authors: ‡Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors: Zhi-Jun
authors: ZJ
authors: Wu
authors: †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: Zhen-Hua
authors: ZH
authors: Wang
authors: †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: Deng-Feng
authors: DF
authors: Yue
authors: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors: Xiao-Ying
authors: XY
authors: Xu
authors: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors: Xiao-Mei
authors: XM
authors: Zhang
authors: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors: Wei-Cheng
authors: WC
authors: Yuan
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D017879:Isothiocyanates; D015394:Molecular Structure; D000078183:Oxindoles; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013859:Thiocarbamates / Q000138:chemical synthesis*
chemical_list: D007211:Indoles; D017879:Isothiocyanates; D000078183:Oxindoles; D011083:Polycyclic Compounds; D013141:Spiro Compounds; D013859:Thiocarbamates; C022960:2-oxindole