Enzyme-catalyzed kinetic resolution of piperidine hydroxy esters

Magdolna Solymár, E. Forró, F. Fülöp

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Enantiomers of N-protected piperidine-based cis- and trans-4-hydroxy-3- carboxylates and cis-3-hydroxy-4-carboxylates were prepared through kinetic resolution utilizing lipase AK from Pseudomonas fluorescens and Candida antarctica lipase A. The highly enantioselective (E >200) kinetic resolution of (±)-ethyl cis-(±)-4 and trans-1-(tert-butoxycarbonyl)-4- hydroxypiperidine-3-carboxylate (±)-5 was achieved by Pseudomonas fluorescens lipase-catalyzed asymmetric acylation with vinyl acetate in diisopropyl ether at room temperature. Candida antarctica lipase A-catalyzed asymmetric acylation of (±)-ethyl cis-1-benzyl-3-hydroxypiperidine-4- carboxylate (±)-11 was performed with vinyl propanoate in diisopropyl ether at 3°C, with good enantioselectivity (E = 75).

Original languageEnglish
Pages (from-to)3281-3287
Number of pages7
JournalTetrahedron Asymmetry
Volume15
Issue number20
DOIs
Publication statusPublished - Oct 18 2004

Fingerprint

Enzyme kinetics
piperidine
Lipases
Lipase
carboxylates
enzymes
esters
Esters
acylation
Acylation
Pseudomonas fluorescens
pseudomonas
Candida
kinetics
Antarctic regions
Enzymes
Ethers
ethers
Enantiomers
Enantioselectivity

ASJC Scopus subject areas

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

Cite this

Enzyme-catalyzed kinetic resolution of piperidine hydroxy esters. / Solymár, Magdolna; Forró, E.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 15, No. 20, 18.10.2004, p. 3281-3287.

Research output: Contribution to journalArticle

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