title: Steroid-Derived Naphthoquinoline Asphaltene Model Compounds: Hydriodic Acid Is the Active Catalyst in I2-Promoted Multicomponent Cyclocondensation Reactions.
abstract: A multicomponent cyclocondensation reaction between 2-aminoanthracene, aromatic aldehydes, and 5-α-cholestan-3-one has been used to synthesize model asphaltene compounds. The active catalyst for this reaction has been identified as hydriodic acid, which is formed in situ from the reaction of iodine with water, while iodine is not a catalyst under anhydrous conditions. The products, which contain a tetrahydro[4]helicene moiety, are optically active, and the stereochemical characteristics have been examined by VT-NMR and VT-CD spectroscopies, as well as X-ray crystallography.
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) , Henkestraße 42, 91054 Erlangen, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Schulze
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, AB T6G 2G2, Canada.
authors.forename: David E
authors.initials: DE
authors.lastname: Scott
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) , Henkestraße 42, 91054 Erlangen, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Scherer
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) , Henkestraße 42, 91054 Erlangen, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Hampel
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, AB T6G 2G2, Canada.
authors.forename: Robin J
authors.initials: RJ
authors.lastname: Hamilton
authors.affiliation: Department of Chemical and Materials Engineering, University of Alberta , Edmonton, Alberta T6G 2 V4, Canada.
authors.forename: Murray R
authors.initials: MR
authors.lastname: Gray
authors.affiliation: Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) , Henkestraße 42, 91054 Erlangen, Germany.
authors.forename: Rik R
authors.initials: RR
authors.lastname: Tykwinski
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, AB T6G 2G2, Canada.
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Stryker
mesh_terms: D000143:Acids / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D000873:Anthracenes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D017613:Iodine Compounds / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*
chemical_list: D000143:Acids; D000447:Aldehydes; D000873:Anthracenes; D017613:Iodine Compounds; D009285:Naphthoquinones; D011084:Polycyclic Aromatic Hydrocarbons; D013256:Steroids; C000592077:asphaltene; C010466:hydroiodic acid; C006593:2-anthramine