Diastereoselective and enantiospecific direct reductive amination in water catalyzed by palladium nanoparticles stabilized by polyethyleneimine derivatives

Noam Levi, Ronny Neumann

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Alkylated polyethylenimine or homochiral polyethylenimine derivatives, or both, were used to stabilize palladium nanoparticles dispersed in water. Such constructs have hydrophobic regions that enabled the aqueous biphasic hydrogenation of imines formed in situ by the reaction of ketones and chiral primary amines. In the presence of MgCl2, good yields of the direct amination product were obtained with high diastereoselectivity. In the presence of a homochiral polyethylenimine, enantiospecific direct amination was observed via kinetic resolution, ostensibly as a result of preferred access of one enantiomer to the achiral reaction center.

Original languageEnglish
Pages (from-to)1915-1918
Number of pages4
JournalACS Catalysis
Volume3
Issue number9
DOIs
Publication statusPublished - Sep 6 2013

Fingerprint

Polyethyleneimine
Amination
Palladium
Nanoparticles
Derivatives
Enantiomers
Water
Ketones
Hydrogenation
Amines
Magnesium Chloride
Imines
Kinetics

Keywords

  • aqueous biphasic catalysis
  • asymmetric catalysis
  • hydrogenation
  • palladium
  • reduction of imines

ASJC Scopus subject areas

  • Catalysis

Cite this

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T1 - Diastereoselective and enantiospecific direct reductive amination in water catalyzed by palladium nanoparticles stabilized by polyethyleneimine derivatives

AU - Levi, Noam

AU - Neumann, Ronny

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N2 - Alkylated polyethylenimine or homochiral polyethylenimine derivatives, or both, were used to stabilize palladium nanoparticles dispersed in water. Such constructs have hydrophobic regions that enabled the aqueous biphasic hydrogenation of imines formed in situ by the reaction of ketones and chiral primary amines. In the presence of MgCl2, good yields of the direct amination product were obtained with high diastereoselectivity. In the presence of a homochiral polyethylenimine, enantiospecific direct amination was observed via kinetic resolution, ostensibly as a result of preferred access of one enantiomer to the achiral reaction center.

AB - Alkylated polyethylenimine or homochiral polyethylenimine derivatives, or both, were used to stabilize palladium nanoparticles dispersed in water. Such constructs have hydrophobic regions that enabled the aqueous biphasic hydrogenation of imines formed in situ by the reaction of ketones and chiral primary amines. In the presence of MgCl2, good yields of the direct amination product were obtained with high diastereoselectivity. In the presence of a homochiral polyethylenimine, enantiospecific direct amination was observed via kinetic resolution, ostensibly as a result of preferred access of one enantiomer to the achiral reaction center.

KW - aqueous biphasic catalysis

KW - asymmetric catalysis

KW - hydrogenation

KW - palladium

KW - reduction of imines

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