Lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-arylpropan-1- ols

Laura Ancua Pop, Andrea Czompa, Csaba Paizs, Monica Ioana Toa, Elemér Vass, Péter Mátyus, Florin Dan Irimie

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-(4- fluorophenyl)propan-1-ol, 3-chloro-1-(4-iodophenyl)propan-1-ol, and 3-chloro-1-phenylpropan-1-ol is described. The procedure is based on the enantiomer-selective acylation of the racemic alcohols in presence of lipase from Pseudomonas fluorescens (LAK) followed by the lipase from Candida rugosa (CRL) mediated hydrolysis of previously obtained enantiomerically enriched 1-aryl-3-chloropropyl esters. For the production of enantiopure (S)-1-aryl-3-chloropropan-1-ols (99% ee, 34-42% yield) the reactions were stopped at higher conversions than the theoretical optimum of 50%, while for enantiopure (R)-1-aryl-3-chloropropyl acetates (99% ee) the reactions were stopped at lower conversions. The latter compounds were enzymatically hydrolyzed into the corresponding (R)-1-aryl-3-chloropropan-1-ols (97-99% ee, 18-24% yield). The absolute configuration of the resolution products was determined by VCD measurements combined with quantum chemical calculations.

Original languageEnglish
Article numberT49711SS
Pages (from-to)2921-2928
Number of pages8
JournalSynthesis
Issue number18
DOIs
Publication statusPublished - Aug 4 2011

    Fingerprint

Keywords

  • alcohols
  • chiral resolution
  • enantioselectivity
  • enzymes
  • halide
  • kinetic resolution

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Pop, L. A., Czompa, A., Paizs, C., Toa, M. I., Vass, E., Mátyus, P., & Irimie, F. D. (2011). Lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-arylpropan-1- ols. Synthesis, (18), 2921-2928. [T49711SS]. https://doi.org/10.1055/s-0030-1260149