Generality-oriented optimization of enantioselective aminoxyl radical catalysis.
basic_science · Level V
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- Record sourced from PubMed, PMID 37200427.
- Also identified by DOI 10.1126/science.adf6177 and PMC identifier 10277815.
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Abstract
Catalytic enantioselective methods that are generally applicable to a broad range of substrates are rare. We report a strategy for the oxidative desymmetrization of <i>meso</i>-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.