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

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 Al2O3 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.