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

4 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

Fingerprint

Proline
Gold
Nanoparticles
Benzaldehydes
Hydroxyproline
Enantioselectivity
Ketones
Catalyst supports
Weight Loss
Ion exchange
Ligands
Derivatives
3-hydroxybutanal
acid gold tetrachloride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions. / Sóti, Péter Lajos; Yamashita, Hiroki; Sato, Kohei; Narumi, Tetsuo; Toda, Mitsuo; Watanabe, Naoharu; Marosi, G.; Mase, Nobuyuki.

In: Tetrahedron, 06.01.2016.

Research output: Article

Sóti, Péter Lajos ; Yamashita, Hiroki ; Sato, Kohei ; Narumi, Tetsuo ; Toda, Mitsuo ; Watanabe, Naoharu ; Marosi, G. ; Mase, Nobuyuki. / Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions. In: Tetrahedron. 2016.
@article{a70e2e8a0ce44a35b48b01a1178db89a,
title = "Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions",
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.",
keywords = "Aldol reaction, Nanoparticle, Organocatalyst, Supported catalysis",
author = "S{\'o}ti, {P{\'e}ter Lajos} and Hiroki Yamashita and Kohei Sato and Tetsuo Narumi and Mitsuo Toda and Naoharu Watanabe and G. Marosi and Nobuyuki Mase",
year = "2016",
month = "1",
day = "6",
doi = "10.1016/j.tet.2016.02.065",
language = "English",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Synthesis of a self-assembling gold nanoparticle-supported organocatalyst for enamine-based asymmetric aldol reactions

AU - Sóti, Péter Lajos

AU - Yamashita, Hiroki

AU - Sato, Kohei

AU - Narumi, Tetsuo

AU - Toda, Mitsuo

AU - Watanabe, Naoharu

AU - Marosi, G.

AU - Mase, Nobuyuki

PY - 2016/1/6

Y1 - 2016/1/6

N2 - 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.

AB - 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.

KW - Aldol reaction

KW - Nanoparticle

KW - Organocatalyst

KW - Supported catalysis

UR - http://www.scopus.com/inward/record.url?scp=84960392539&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84960392539&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.02.065

DO - 10.1016/j.tet.2016.02.065

M3 - Article

AN - SCOPUS:84960392539

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -