title: Catalytic asymmetric Povarov reaction of isatin-derived 2-azadienes with 3-vinylindoles.
abstract: The first catalytic asymmetric Povarov reaction of isatin-derived 2-azadienes with 3-vinylindoles was established in the presence of chiral phosphoric acid, which tolerates a wide range of substrates with generally excellent diastereoselectivity and good enantioselectivity (up to >95 : 5 dr, 89 : 11 er). This approach will greatly enrich the chemistry of the catalytic asymmetric Povarov reaction, in particular ketone-involved transformations. Furthermore, this protocol represents the first diastereo- and enantio-selective construction of a spiro[indolin-3,2'-quinoline] framework bearing an indole moiety. This novel type of spiro-compound not only contains two chiral centers, including one quaternary stereogenic center, but also integrates two biologically important structures of spiro[indolin-3,2'-quinoline] and indole, which may find medicinal applications after bioassay.
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China. fshi@jsnu.edu.cn zcch@163.com.
authors.forename: Hong-Hao
authors.initials: HH
authors.lastname: Zhang
authors.forename: Xiao-Xue
authors.initials: XX
authors.lastname: Sun
authors.forename: Jing
authors.initials: J
authors.lastname: Liang
authors.forename: Yue-Ming
authors.initials: YM
authors.lastname: Wang
authors.forename: Chang-Chun
authors.initials: CC
authors.lastname: Zhao
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D008958:Models, Molecular; D010756:Phosphoric Acids / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D010756:Phosphoric Acids; D013141:Spiro Compounds; C057812:indoline; D007510:Isatin; C030242:phosphoric acid