Dynamic Kinetic Resolution of <i>rac</i>‐2‐Hydroxy‐1‐indanone by using a Heterogeneous Ru(OH)₃/Al₂O₃ Racemization Catalyst and Lipase

Abstract

Abstract Kinetic resolution and dynamic kinetic resolution, in particular, provide practical tools for synthesis of enantiomerically pure compounds. In the present work, the resolution of rac ‐2‐hydroxy‐1‐indanone and racemization of ( S )‐2‐hydroxy‐1‐indanone were investigated. Immobilized lipase AK ( Pseudomonas fluorescens ) was found as the best enzyme catalyst for kinetic resolution and ruthenium supported on Al 2 O 3 as a potential heterogeneous catalyst for racemization of the starting material. By combining the two reactions, a simple dynamic kinetic resolution of rac ‐2‐hydroxy‐1‐indanone producing ( R )‐1‐oxo‐indan‐2‐yl butanoate was developed. Under optimal conditions, the product was obtained in 92 % ee at approximately 90 % conversion.