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

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Langvik O, Saloranta T, Kirilin A, Liljeblad A, Maki-Arvela P, Kanerva LT, Murzin DY, Leino R
Publisher: WILEY-BLACKWELL
Publication year: 2010
Journal: ChemCatChem
Journal acronym: CHEMCATCHEM
Volume number: 2
Issue number: 12
Start page: 1615
End page: 1621
Number of pages: 7
ISSN: 1867-3880


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 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-oxoindan-2-yl butanoate was developed. Under optimal conditions, the product was obtained in 92% ee at approximately 90% conversion.


Keywords

dynamic kinetic resolution, enzyme catalysis, heterogeneous catalysis, ruthenium, supported catalysts

Last updated on 2019-22-11 at 02:51