Benzoxaboroles, prominent scaffolds in medicinal chemistry, are typically modified on the benzene ring. In contrast, functionalization of the oxaborol ring is less common and often challenging. Indeed, 3-hydroxy-benzoxaboroles are virtually impossible to isolate due to their tautomeric equilibrium with the carbonyl form. In this work, we introduce a novel class of stereodefined 3-difluoromethyl-benzoxaboroles. The replacement of the hydroxy group with −CHF2 preserves stability while promoting bioactivity, owing to the lipophilic H-bond donor properties of the latter.
Stereodefined Synthesis of 3-Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H-Bonding / Dimasi, A., Montoli, A., Lutti, C., Citarella, A., Ronchi, P., Castagnini, F., Mileo, V., Macetti, G., Baldelli, V., Rossi, E., Landini, P., Passarella, D., Fasano, V.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 28:5(2026), pp. 1527-1532. [10.1021/acs.orglett.5c04602]
Stereodefined Synthesis of 3-Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H-Bonding
Castagnini, Francesco;
2026-01-01
Abstract
Benzoxaboroles, prominent scaffolds in medicinal chemistry, are typically modified on the benzene ring. In contrast, functionalization of the oxaborol ring is less common and often challenging. Indeed, 3-hydroxy-benzoxaboroles are virtually impossible to isolate due to their tautomeric equilibrium with the carbonyl form. In this work, we introduce a novel class of stereodefined 3-difluoromethyl-benzoxaboroles. The replacement of the hydroxy group with −CHF2 preserves stability while promoting bioactivity, owing to the lipophilic H-bond donor properties of the latter.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
