title: Electroreductive intermolecular coupling of 3-methoxycarbonylindoles with ketones.
abstract: The electroreductive coupling of 1-alkoxycarbonyl-3-methoxycarbonylindoles with aromatic ketones in the presence of chlorotrimethylsilane gave cis-adducts stereoselectively. The cis-adducts were readily transformed to trans-adducts by treatment with catalyst DBU. On the other hand, the electroreductive coupling of 1-methyl-3-methoxycarbonylindole with aliphatic ketones in isopropanol afforded trans-adducts exclusively. The adducts are the precursors for the synthesis of 2-substituted 3-methoxycarbonylindoles and indolines.
authors.affiliation: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp
authors.forename: Naoki
authors.initials: N
authors.lastname: Kise
authors.forename: Akinori
authors.initials: A
authors.lastname: Sueyoshi
authors.forename: Shin-ichirou
authors.initials: S
authors.lastname: Takeuchi
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Sakurai
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D007211:Indoles; D007659:Ketones; D014297:Trimethylsilyl Compounds; C039293:trimethylchlorosilane; C057812:indoline