Generality-oriented optimization of enantioselective aminoxyl radical catalysis
Catalytic enantioselective methods that are generally applicable to a broad range of substrates are rare. We report a strategy for the oxidative desymmetrization of -diols predicated on a nontraditional catalyst optimization protocol by using a panel of screening substrates rather than a singular mo...
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Veröffentlicht in: | Science (American Association for the Advancement of Science) 2023-05, Vol.380 (6646), p.706-712 |
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Hauptverfasser: | , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Catalytic enantioselective methods that are generally applicable to a broad range of substrates are rare. We report a strategy for the oxidative desymmetrization of
-diols predicated on a nontraditional catalyst optimization protocol by using a panel of screening substrates rather than a singular model substrate. Critical to this approach was rational modulation of a peptide sequence in the catalyst incorporating a distinct aminoxyl-based active residue. A general catalyst emerged, providing high selectivity in the delivery of enantioenriched lactones across a broad range of diols, while also achieving up to ~100,000 turnovers. |
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ISSN: | 0036-8075 1095-9203 |
DOI: | 10.1126/science.adf6177 |