Development of Catalytic Reactions for Precise Control of Chemoselectivity

Catalytic chemoselective reactions of innately less reactive functionalities over more reactive functionalities are described. A cooperative catalyst comprising a soft Lewis acid/hard Bronsted base enabled chemoselective activation of a hydroxyl group over an amino group, allowing for nucleophilic addition to electron-deficient olefins. The reaction could be applicable for a variety of amino alcohols, including pharmaceuticals, without requiring a tedious protection-deprotection process. Chemoselective enolization and subsequent alpha-functionalization of carboxylic acid derivatives were also achieved by a redox active catalyst through the radical process, providing unnatural alpha-amino/hydroxy acid derivatives bearing a complex carbon framework and a diverse set of functionalities. The present chemoselective catalysis described herein offers new opportunities to expand the chemical space for innovative drug discovery research.

Automated summary

The described catalytic chemoselective reactions enable selective activation of less reactive functionalities over more reactive ones, allowing for efficient synthesis of complex molecules without the need for tedious protection-deprotection processes. This offers new opportunities for innovative drug discovery research by expanding the chemical space available for exploration.