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

Research output: Contribution to journalArticleScientificpeer-review

12 Citations (Scopus)

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.
Original languageUndefined/Unknown
Pages (from-to)1615–1621
Number of pages7
JournalChemCatChem
Volume2
Issue number12
DOIs
Publication statusPublished - 2010
MoE publication typeA1 Journal article-refereed

Keywords

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

Cite this