Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

Csaba Paizs, Monica Toşa, Viktória Bódai, G. Szakács, Ildikó Kmecz, B. Simándi, Cornelia Majdik, L. Novák, Florin Dan Irimie, L. Poppe

Research output: Contribution to journalArticle

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Abstract

Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (E≫100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanols (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d.

Original languageEnglish
Pages (from-to)1943-1949
Number of pages7
JournalTetrahedron Asymmetry
Volume14
Issue number13
DOIs
Publication statusPublished - Jul 4 2003

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Enantiomers
enantiomers
Lipases
Ethane
Lipase
ethane
Ethanol
ethyl alcohol
Kinetics
kinetics
acylation
Acylation
Enzyme kinetics
Enzymatic hydrolysis
hydrolysis
selectivity
1-benzofuran
Hydrolysis

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions. / Paizs, Csaba; Toşa, Monica; Bódai, Viktória; Szakács, G.; Kmecz, Ildikó; Simándi, B.; Majdik, Cornelia; Novák, L.; Irimie, Florin Dan; Poppe, L.

In: Tetrahedron Asymmetry, Vol. 14, No. 13, 04.07.2003, p. 1943-1949.

Research output: Contribution to journalArticle

Paizs, Csaba ; Toşa, Monica ; Bódai, Viktória ; Szakács, G. ; Kmecz, Ildikó ; Simándi, B. ; Majdik, Cornelia ; Novák, L. ; Irimie, Florin Dan ; Poppe, L. / Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions. In: Tetrahedron Asymmetry. 2003 ; Vol. 14, No. 13. pp. 1943-1949.
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