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

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Publikationens författare: Langvik O, Saloranta T, Kirilin A, Liljeblad A, Maki-Arvela P, Kanerva LT, Murzin DY, Leino R
Förläggare: WILEY-BLACKWELL
Publiceringsår: 2010
Tidskrift: ChemCatChem
Tidskriftsakronym: CHEMCATCHEM
Volym: 2
Nummer: 12
Artikelns första sida, sidnummer: 1615
Artikelns sista sida, sidnummer: 1621
Antal sidor: 7
ISSN: 1867-3880


Abstrakt

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.


Nyckelord

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

Senast uppdaterad 2020-26-02 vid 05:39