Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions

Péter Lajos Sóti, Hiroki Yamashita, Kohei Sato, Tetsuo Narumi, Mitsuo Toda, Naoharu Watanabe, G. Marosi, Nobuyuki Mase

Research output: Article

5 Citations (Scopus)

Abstract

The self-assembling gold nanoparticle (GNP)-supported . l-proline derivative, which was readily synthesized in four steps from 4-hydroxy-l-proline and chloroauric acid, was used for enamine-based aldol reactions. The modified Brust-Schiffrin (BS) synthesis was favored over the ligand exchange reaction in order to develop a new and simple synthetic pathway for nanoparticle-supported catalyst. Use of immobilized organocatalyst on nanoscale solid carrier led to excellent selectivities (up to 94:6 dr and 94% ee) in asymmetric reactions of ketones and benzaldehydes. GNPs operate under pseudo-homogeneous conditions which are easily recycled and reused at least five times without significant loss of weight, activity, diastereo- and enantioselectivities.

Original languageEnglish
JournalTetrahedron
DOIs
Publication statusAccepted/In press - jan. 6 2016

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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