Reductive transamination of methoxyacetone with benzylamine over Pd/SiO2 catalyst modified with anchored chiral compounds

S. Göbölös, E. Tálas, E. Tfirst, J. L. Margitfalvi, K. S. Hayes

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Methoxyacetone was transaminated with benzylamine to methoxyisopropylamine over a Pd/SiO2 catalyst modified with L-alaninol or L-phenylalaninol covalently anchored to the surface of the support via an organo-silicon spacer group. In the first step of transamination a Schiff base was formed from the ketone and benzylamine, and then it was hydrogenated in the second step on the chirally modified Pd/SiO2 catalysts to an asymmetric secondary amine (N-benzyl-methoxyisopropylamine). In the third step the hydrogenolysis of the asymmetric secondary amine resulting in methoxyisopropylamine and toluene was carried out over a 10 wt% Pd/C catalyst. The highest enantiomeric excess of (S)-methoxyisopropylamine was observed in cyclohexane (ee = -20-21%) using anchored L-alaninol as a chiral modifier.

Original languageEnglish
Pages (from-to)143-149
Number of pages7
JournalCatalysis Letters
Volume61
Issue number3-4
Publication statusPublished - Sep 1999

Fingerprint

catalysts
Catalysts
Amines
amines
hydrogenolysis
Hydrogenolysis
Schiff Bases
Toluene
Silicon
Cyclohexane
Ketones
ketones
cyclohexane
spacers
imines
toluene
silicon
benzylamine
2-aminopropanol
phenylalaninol

Keywords

  • Chiral modifiers
  • Enantioselective amination
  • Enantioselective hydrogenation
  • Methoxyacetone
  • Methoxyisopropylamine
  • Palladium catalysts
  • Reductive transamination
  • Schiff base

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

Reductive transamination of methoxyacetone with benzylamine over Pd/SiO2 catalyst modified with anchored chiral compounds. / Göbölös, S.; Tálas, E.; Tfirst, E.; Margitfalvi, J. L.; Hayes, K. S.

In: Catalysis Letters, Vol. 61, No. 3-4, 09.1999, p. 143-149.

Research output: Contribution to journalArticle

Göbölös, S. ; Tálas, E. ; Tfirst, E. ; Margitfalvi, J. L. ; Hayes, K. S. / Reductive transamination of methoxyacetone with benzylamine over Pd/SiO2 catalyst modified with anchored chiral compounds. In: Catalysis Letters. 1999 ; Vol. 61, No. 3-4. pp. 143-149.
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AU - Göbölös, S.

AU - Tálas, E.

AU - Tfirst, E.

AU - Margitfalvi, J. L.

AU - Hayes, K. S.

PY - 1999/9

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N2 - Methoxyacetone was transaminated with benzylamine to methoxyisopropylamine over a Pd/SiO2 catalyst modified with L-alaninol or L-phenylalaninol covalently anchored to the surface of the support via an organo-silicon spacer group. In the first step of transamination a Schiff base was formed from the ketone and benzylamine, and then it was hydrogenated in the second step on the chirally modified Pd/SiO2 catalysts to an asymmetric secondary amine (N-benzyl-methoxyisopropylamine). In the third step the hydrogenolysis of the asymmetric secondary amine resulting in methoxyisopropylamine and toluene was carried out over a 10 wt% Pd/C catalyst. The highest enantiomeric excess of (S)-methoxyisopropylamine was observed in cyclohexane (ee = -20-21%) using anchored L-alaninol as a chiral modifier.

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KW - Chiral modifiers

KW - Enantioselective amination

KW - Enantioselective hydrogenation

KW - Methoxyacetone

KW - Methoxyisopropylamine

KW - Palladium catalysts

KW - Reductive transamination

KW - Schiff base

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