Efficient Iron-Catalyzed Site/Regioselective Phosphinoylation of Carbohydrates

Org Lett. 2025 Feb 14;27(6):1555-1560. doi: 10.1021/acs.orglett.5c00143. Epub 2025 Jan 31.

Abstract

The selective incorporation of phosphorus groups into sugar molecules holds substantial synthetic and biological significance, yet this area of research remains largely unexplored. In this study, we successfully devised a novel method employing an efficient Fe(III) catalyst for achieving site/regioselective phosphorylation/phosphinoylation of carbohydrates. This methodology boasts several merits, including mild reaction conditions, the employment of cost-effective and readily available catalysts, and exceptional selectivity. This approach provides new perspectives and valuable tools for the functional modification of sugar molecules.