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Nucleophilic aromatic substitutions enable diversity-oriented synthesis of heterocyclic atropisomers via non-atropisomeric intermediates
Nature Communications 16: 4856 (2025)
Atropisomers are sterically hindered molecules whose formation typically proceeds via atropisomeric intermediates and encumbered transition states. It is therefore largely accepted that the activation energy is higher for synthesis of atropisomers than for synthesis of similar, less sterically congested non-atropisomeric compounds. Here we show that atropisomer formation by nucleophilic aromatic substitution (SNAr) reactions can progress via non-atropisomeric intermediates and transition states. We put forth fast, mild, practical, regio- and chemoselective SNAr reactions that generate a diverse array of difficult-to-access heterobiaryl C─N atropisomers starting with readily available N─H heterocycles and aryl fluorides, as well as two catalytic methods employing N─SiR3 and N─H heterocycles for synthesis of title atropisomers in seconds. Products of SNAr are readily diversifiable, streamlining access to countless drug-like C─N atropisomers, including macrocycles, peptides, and analogs…
On-Resin Assembly of Macrocyclic Inhibitors of Cryptococcus neoformans May1: A Pathway to Potent Antifungal Agents
Journal of Medicinal Chemistry 68 (9): 9623–9637 (2025)
Bacterial Fluorinase FIA1 and Evolutionarily Related, Lysine-free StDUF62 Show Distinct Diastereoselectivity and Salt Sensitivity
ACS Omega 10 (20): 20509–20514 (2025)
Peptide Analysis by Soft X-ray Atmospheric Pressure Photoionization Mass Spectrometry
Journal of the American Society for Mass Spectrometry 2025: Early View