Chemoselective and Enantioselective Oxidation of Indoles Employing Aspartyl Peptide Catalysts
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Movassaghi_Chemoselective and.pdf
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2.57 MB
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Author(s)
Movassaghi, Mohammad
Noshi Alhanafy, Mohammad N.
Tjandra, Meiliana
Miller, Scott J.
Kolundzic, Filip
Date Issued
May 2011
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Kolundzic, Filip et al. “Chemoselective and Enantioselective Oxidation of Indoles Employing Aspartyl Peptide Catalysts.” Journal of the American Chemical Society 133.23 (2011): 9104–9111.
Version
Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja202706g
