Steroid-Derived Naphthoquinoline Asphaltene Model Compounds: Hydriodic Acid Is the Active Catalyst in I-2-Promoted Multicomponent Cyclocondensation Reactions
Schulze M, Scott DE, Scherer A, Hampel F, Hamilton RJ, Gray MR, Tykwinski R, Stryker JM (2015)
Publication Language: English
Publication Status: Published
Publication Type: Journal article
Publication year: 2015
Journal
Publisher: American Chemical Society
Book Volume: 17
Pages Range: 5930-5933
Journal Issue: 23
DOI: 10.1021/acs.orglett.5b03193
Abstract
A multicomponent cydocondensation reaction between 2-aminoanthracene, aromatic aldehydes, and 5-alpha-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 with CRIS profile
Matthias Schulze
Lehrstuhl für Organische Chemie I
Alexander Scherer
Lehrstuhl für Organische Chemie I
Frank Hampel
Lehrstuhl für Organische Chemie I
Rik Tykwinski
Lehrstuhl für Organische Chemie I
Involved external institutions
Canada (CA)How to cite
APA:
Schulze, M., Scott, D.E., Scherer, A., Hampel, F., Hamilton, R.J., Gray, M.R.,... Stryker, J.M. (2015). Steroid-Derived Naphthoquinoline Asphaltene Model Compounds: Hydriodic Acid Is the Active Catalyst in I-2-Promoted Multicomponent Cyclocondensation Reactions. Organic Letters, 17(23), 5930-5933. https://doi.org/10.1021/acs.orglett.5b03193
MLA:
Schulze, Matthias, et al. "Steroid-Derived Naphthoquinoline Asphaltene Model Compounds: Hydriodic Acid Is the Active Catalyst in I-2-Promoted Multicomponent Cyclocondensation Reactions." Organic Letters 17.23 (2015): 5930-5933.
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