Late-Stage Chemo- and Enantioselective Oxidation of Indoles to C3-Monosubstituted Oxindoles
Catalytic asymmetric preparation of chiral 3-monosubstituted oxindoles represents a significant challenge in synthetic chemistry due to the ease of racemization of the tertiary stereocenter through enolization. Here, we describe a general titanium-catalyzed chemo- and enantioselective indole oxidation to produce a diverse set of chiral 3-monosubstituted oxindoles with up to 96% yield, 99% ee, and with a substrate/catalyst ratio of 10,000 by using the combination of a simple titanium(salan) catalyst with green and atom-economic terminal oxidant H2O2. The mild approach tolerates a broad range of functional groups, enabling late-stage asymmetric diversification of a series of commercial drugs and natural products together with late-stage asymmetric construction of a wide set of enzyme antagonists, all of which are difficult to achieve through existing methods.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:145 |
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| Enthalten in: |
Journal of the American Chemical Society - 145(2023), 49 vom: 13. Dez., Seite 27120-27130 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Song [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 13.12.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/jacs.3c11742 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Catalytic asymmetric preparation of chiral 3-monosubstituted oxindoles represents a significant challenge in synthetic chemistry due to the ease of racemization of the tertiary stereocenter through enolization. Here, we describe a general titanium-catalyzed chemo- and enantioselective indole oxidation to produce a diverse set of chiral 3-monosubstituted oxindoles with up to 96% yield, 99% ee, and with a substrate/catalyst ratio of 10,000 by using the combination of a simple titanium(salan) catalyst with green and atom-economic terminal oxidant H2O2. The mild approach tolerates a broad range of functional groups, enabling late-stage asymmetric diversification of a series of commercial drugs and natural products together with late-stage asymmetric construction of a wide set of enzyme antagonists, all of which are difficult to achieve through existing methods | ||
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