Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4- phenylpyrrolidine

F. Faigl, Ervin Kovács, Dóra Balogh, Tamás Holczbauer, M. Czugler, B. Simándi

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The first enzyme-catalyzed kinetic resolution of tert-butyl-3-hydroxy-4- phenylpyrrolidine-1-carboxylate is presented. Enzyme, solvent and temperature optimization resulted in a new resolution method with E = 40 enantioselectivity. The acetate derivative of the (+)-(3S,4R) enantiomer formed while the (-)-(3R,4S) isomer remained intact. Very good enantioselectivities (E > 200) were achieved in the enzyme-catalyzed alcoholysis of the racemic acetate in i-propanol and t-butanol where the (+)-(3S,4R) enantiomer was prepared in pure form (ee > 99.7%). Absolute configuration of the (-)-(3R,4S)-enantiomer was determined by single crystal X-ray diffraction method. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)25-32
Number of pages8
JournalCentral European Journal of Chemistry
Volume12
Issue number1
DOIs
Publication statusPublished - Jan 2014

Fingerprint

Enzyme kinetics
Enantiomers
Enantioselectivity
Acetates
Enzymes
tert-Butyl Alcohol
1-Propanol
Propanol
Butenes
Isomers
Single crystals
Derivatives
X ray diffraction
Temperature

Keywords

  • 3-hydroxy-4-phenylpyrrolidine
  • Enantioselective alcoholysis
  • Enzymatic hydrolysis
  • Enzyme-catalyzed resolution
  • Lipase enzymes

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

Cite this

Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4- phenylpyrrolidine. / Faigl, F.; Kovács, Ervin; Balogh, Dóra; Holczbauer, Tamás; Czugler, M.; Simándi, B.

In: Central European Journal of Chemistry, Vol. 12, No. 1, 01.2014, p. 25-32.

Research output: Contribution to journalArticle

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AU - Kovács, Ervin

AU - Balogh, Dóra

AU - Holczbauer, Tamás

AU - Czugler, M.

AU - Simándi, B.

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N2 - The first enzyme-catalyzed kinetic resolution of tert-butyl-3-hydroxy-4- phenylpyrrolidine-1-carboxylate is presented. Enzyme, solvent and temperature optimization resulted in a new resolution method with E = 40 enantioselectivity. The acetate derivative of the (+)-(3S,4R) enantiomer formed while the (-)-(3R,4S) isomer remained intact. Very good enantioselectivities (E > 200) were achieved in the enzyme-catalyzed alcoholysis of the racemic acetate in i-propanol and t-butanol where the (+)-(3S,4R) enantiomer was prepared in pure form (ee > 99.7%). Absolute configuration of the (-)-(3R,4S)-enantiomer was determined by single crystal X-ray diffraction method. [Figure not available: see fulltext.]

AB - The first enzyme-catalyzed kinetic resolution of tert-butyl-3-hydroxy-4- phenylpyrrolidine-1-carboxylate is presented. Enzyme, solvent and temperature optimization resulted in a new resolution method with E = 40 enantioselectivity. The acetate derivative of the (+)-(3S,4R) enantiomer formed while the (-)-(3R,4S) isomer remained intact. Very good enantioselectivities (E > 200) were achieved in the enzyme-catalyzed alcoholysis of the racemic acetate in i-propanol and t-butanol where the (+)-(3S,4R) enantiomer was prepared in pure form (ee > 99.7%). Absolute configuration of the (-)-(3R,4S)-enantiomer was determined by single crystal X-ray diffraction method. [Figure not available: see fulltext.]

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