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

Otto Långvik, Tiina Saloranta, Alexey Kirilin, A Liljeblad, Päivi Mäki-Arvela, LT Kanerva, Dmitry Murzin, Reko Leino

Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

13 Citeringar (Scopus)

Sammanfattning

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.
OriginalspråkOdefinierat/okänt
Sidor (från-till)1615–1621
Antal sidor7
TidskriftChemCatChem
Volym2
Utgåva12
DOI
StatusPublicerad - 2010
MoE-publikationstypA1 Tidskriftsartikel-refererad

Nyckelord

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

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