title: Organocatalytic stereocontrolled synthesis of 3,3'-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones.
abstract: A stereoselective [3+2] cycloaddition of isocyanoesters to methyleneindolinones catalyzed by a quinine-based thiourea-tertiary amine has been successfully developed. Just by tuning the protecting groups on substrates, a variety of optically enriched 3,3'-pyrrolidinyl spirooxindole diastereomers could be obtained in excellent enantioselectivities (up to 99% ee).
authors.affiliation: Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Liang-Liang
authors.initials: LL
authors.lastname: Wang
authors.forename: Jian-Fei
authors.initials: JF
authors.lastname: Bai
authors.forename: Lin
authors.initials: L
authors.lastname: Peng
authors.forename: Liang-Wen
authors.initials: LW
authors.lastname: Qi
authors.forename: Li-Na
authors.initials: LN
authors.lastname: Jia
authors.forename: Yun-Long
authors.initials: YL
authors.lastname: Guo
authors.forename: Xi-Ya
authors.initials: XY
authors.lastname: Luo
authors.forename: Xiao-Ying
authors.initials: XY
authors.lastname: Xu
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Wang
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000737:chemistry*; D011803:Quinine / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D000588:Amines; D007211:Indoles; D011759:Pyrrolidines; D011803:Quinine; D013890:Thiourea; C032519:pyrrolidine