Work

Generality-oriented optimization of enantioselective aminoxyl radical catalysis

Year: 2023

Type: article

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 meso -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.

Source: Science

DOI: 10.1126/science.adf6177

Authors: Jonas Rein, Soren D. Rozema, Olivia C. Langner, Samson B. Zacate, Melissa A. Hardy, Juno C. Siu, Brandon Q. Mercado, Matthew S. Sigman, Scott J. Miller, Song Lin

Institutions: Cornell University, Yale University, University of Utah

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Pfizer, Yale University, University of Utah, Studienstiftung des Deutschen Volkes, Center for High Performance Computing, National Institute of General Medical Sciences, Division of Chemistry

Awards: G1134277896, G2921725335, G3290007203, MRI: Acquisition of a Cryogenic Probe and Modern Console for Outstanding NMR Sensitivity to Benefit Research and Education at Cornell University, G8389919011, Site-Selective Catalysis for Bioactive Scaffold Diversification

OpenAlex ID: W4377013954

FWCI: 9.929

Cites: 86

Cited by: 97

Related to: 10