Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Br??nsted acid-catalyzed C???O bond cleavage through an achiral carbocation intermediate. Superscript/Subscript Available

Automated summary

This study demonstrates the racemization of enantiomerically pure alcohols using 2-carboxyphenylboronic acid and oxalic acid as catalysts in the presence of 2-butanone as a solvent. The process involves reversible Br??nsted acid-catalyzed C???O bond cleavage and the formation of an achiral carbocation intermediate.