Generality-Oriented Optimization of Enantioselective Aminoxyl Radical Catalysis

07 November 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Catalytic enantioselective methods that are general over a broad range of substrates facilitate application in synthetic discovery and development settings; however, truly general catalysts for asymmetric synthesis are rare. Herein, we report a strategy for the oxidative desymmetrization of meso-1,4 diols predicated on a non-traditional optimization protocol utilizing a panel of screening substrates rather than a singular model substrate. Critical to this approach was rational modulation of a peptide sequence incorporating a novel, aminoxyl-based catalytic residue. A general catalyst emerged, providing high selectivity in delivery of enantioenriched lactones across a broad range of diols.

Keywords

Generality-oriented optimization
Asymmetric catalysis
Aminoxyl radicals
Peptide catalysis
chiral lactones
Alcohol oxidation
High-throughput experimentation

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