Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of β-lactams

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Abstract

1,4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.02.5]nonan-4-one, (±)-1, and exo-3-azatricyclo[4.2.1.02.5]non-7-en-4-one, (±)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1equiv of H2O in diisopropyl ether at 70°C. The resolved β-amino acids 1a and 2a (yield 46%) and β-lactams 1b and 2b (yield≥40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding β-amino acid hydrochloride enantiomers (ee ≥98%).

Original languageEnglish
Pages (from-to)573-575
Number of pages3
JournalTetrahedron Asymmetry
Volume15
Issue number4
DOIs
Publication statusPublished - Feb 23 2004

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Lactams
Enantiomers
enantiomers
Lipases
Lipase
Ethylene
ethylene
Amino Acids
amino acids
Amino acids
rings
synthesis
Enantioselectivity
hydrochlorides
Ethers
ethers
cispentacin
diisopropyl ether

ASJC Scopus subject areas

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

Cite this

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title = "Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of β-lactams",
abstract = "1,4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.02.5]nonan-4-one, (±)-1, and exo-3-azatricyclo[4.2.1.02.5]non-7-en-4-one, (±)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1equiv of H2O in diisopropyl ether at 70°C. The resolved β-amino acids 1a and 2a (yield 46{\%}) and β-lactams 1b and 2b (yield≥40{\%}) could be easily separated. The ring opening of lactam enantiomers with 18{\%} HCl afforded the corresponding β-amino acid hydrochloride enantiomers (ee ≥98{\%}).",
author = "E. Forr{\'o} and F. F{\"u}l{\"o}p",
year = "2004",
month = "2",
day = "23",
doi = "10.1016/j.tetasy.2003.12.034",
language = "English",
volume = "15",
pages = "573--575",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "4",

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TY - JOUR

T1 - Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of β-lactams

AU - Forró, E.

AU - Fülöp, F.

PY - 2004/2/23

Y1 - 2004/2/23

N2 - 1,4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.02.5]nonan-4-one, (±)-1, and exo-3-azatricyclo[4.2.1.02.5]non-7-en-4-one, (±)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1equiv of H2O in diisopropyl ether at 70°C. The resolved β-amino acids 1a and 2a (yield 46%) and β-lactams 1b and 2b (yield≥40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding β-amino acid hydrochloride enantiomers (ee ≥98%).

AB - 1,4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.02.5]nonan-4-one, (±)-1, and exo-3-azatricyclo[4.2.1.02.5]non-7-en-4-one, (±)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1equiv of H2O in diisopropyl ether at 70°C. The resolved β-amino acids 1a and 2a (yield 46%) and β-lactams 1b and 2b (yield≥40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding β-amino acid hydrochloride enantiomers (ee ≥98%).

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U2 - 10.1016/j.tetasy.2003.12.034

DO - 10.1016/j.tetasy.2003.12.034

M3 - Article

VL - 15

SP - 573

EP - 575

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 4

ER -