Synthesis and recovery of pyridine-and piperidine-based camphorsulfonamide organocatalysts used for michael addition reaction

Péter Kisszékelyi, Sándor Nagy, Blanka Tóth, Bálint Zeller, L. Hegedûs, Béla Mátravölgyi, A. Grün, T. Németh, P. Huszthy, József Kupai

Research output: Contribution to journalArticle

Abstract

Two new pyridine-based asymmetric bifunctional organocatalysts containing one or two camphorsulfonamide units were synthesized. Asymmetric Michael addition of pentane-2,4-dione to β-nitrostyrene was catalyzed by these organocatalysts. During our experiments, influence of the solvent and temperature on the yield and enantioselectivity was studied. Using monocamphorsulfonamide derivative the S enantiomer of the corresponding Michael adduct was gained with moderate yield (up to 51 %) and low enantiomeric excess (up to 18 %). Organic solvent nanofiltration was successfully applied for the recovery of these organocatalysts. Furthermore, pyridine camphorsulfonamide was reduced to its piperidine derivative. Using piperidine monosulfonamide derivative racemic Michael adduct was obtained with excellent yield (up to 89 %). Beside its organocatalytic relevance, piperidine monosulfonamide derivative may also possess biological activity.

Original languageEnglish
Pages (from-to)489-496
Number of pages8
JournalPeriodica Polytechnica Chemical Engineering
Volume62
Issue number4
DOIs
Publication statusPublished - Nov 20 2018

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Addition reactions
Pyridine
Derivatives
Recovery
Nanofiltration
Enantiomers
Enantioselectivity
Bioactivity
Organic solvents
piperidine
pyridine
Experiments
Temperature

Keywords

  • Asymmetric synthesis
  • Camphorsulfonamide
  • Catalyst recovery
  • Michael addition
  • Organocatalyst

ASJC Scopus subject areas

  • Chemical Engineering(all)

Cite this

Synthesis and recovery of pyridine-and piperidine-based camphorsulfonamide organocatalysts used for michael addition reaction. / Kisszékelyi, Péter; Nagy, Sándor; Tóth, Blanka; Zeller, Bálint; Hegedûs, L.; Mátravölgyi, Béla; Grün, A.; Németh, T.; Huszthy, P.; Kupai, József.

In: Periodica Polytechnica Chemical Engineering, Vol. 62, No. 4, 20.11.2018, p. 489-496.

Research output: Contribution to journalArticle

Kisszékelyi, Péter ; Nagy, Sándor ; Tóth, Blanka ; Zeller, Bálint ; Hegedûs, L. ; Mátravölgyi, Béla ; Grün, A. ; Németh, T. ; Huszthy, P. ; Kupai, József. / Synthesis and recovery of pyridine-and piperidine-based camphorsulfonamide organocatalysts used for michael addition reaction. In: Periodica Polytechnica Chemical Engineering. 2018 ; Vol. 62, No. 4. pp. 489-496.
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AU - Zeller, Bálint

AU - Hegedûs, L.

AU - Mátravölgyi, Béla

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AU - Huszthy, P.

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