Chemoselective and enantioselective oxidation of indoles employing aspartyl peptide catalysts.
| Autor: | Kolundzic F; Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA., Noshi MN, Tjandra M, Movassaghi M, Miller SJ |
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| Jazyk: | angličtina |
| Zdroj: | Journal of the American Chemical Society [J Am Chem Soc] 2011 Jun 15; Vol. 133 (23), pp. 9104-11. Date of Electronic Publication: 2011 May 23. |
| DOI: | 10.1021/ja202706g |
| Abstrakt: | Catalytic enantioselective indole oxidation is a process of particular relevance to the chemistry of complex alkaloids, as it has been implicated in their biosynthesis. In the context of synthetic methodology, catalytic enantioselective indole oxidation allows a rapid and biomimetic entry into several classes of alkaloid natural products. Despite this potentially high utility in the total synthesis, reports of catalytic enantioselective indole oxidation remain sparse. Here we report a highly chemoselective catalytic system for the indole oxidation that delivers 3-hydroxy-indolenines with good chemical yields and moderate to high levels of enantio- and diastereoselectivity (up to 95:5 er and up to 92:8 dr). These results represent, to our knowledge, the most selective values yet reported in the literature for catalytic asymmetric indole oxidation. Furthermore, the utility of enantioenriched hydroxy-indolenines in stereospecific rearrangements is demonstrated. (© 2011 American Chemical Society) |
| Databáze: | MEDLINE |
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