title: FeCl3-catalyzed stereoselective construction of spirooxindole tetrahydroquinolines via tandem 1,5-hydride transfer/ring closure.
abstract: An efficient FeCl(3)-catalyzed stereoselective intramolecular tandem 1,5-hydride transfer/ring closure reaction was developed. The method allows for the formation of structurally diverse spirooxindole tetrahydroquinolines in high yields (up to 98%) with good to excellent levels of diastereoselectivity (up to 99:1 dr). The catalytic enantioselective variant of this process was also investigated preliminarily with a chiral BINOL-derived phosphoric acid.
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Yan-Yan
authors.initials: YY
authors.lastname: Han
authors.forename: Wen-Yong
authors.initials: WY
authors.lastname: Han
authors.forename: Xue
authors.initials: X
authors.lastname: Hou
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005290:Ferric Compounds / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C406944:BINOL, naphthol; D002712:Chlorides; D005290:Ferric Compounds; D007211:Indoles; D009284:Naphthols; D011804:Quinolines; D013141:Spiro Compounds; C542964:1,2,3,4-tetrahydroquinoline; C024555:ferric chloride