Sugar-based crown ethers in enantioselective syntheses

P. Bakó, Zsolt Rapi, G. Keglevich

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A number of chiral macrocyclic compounds have been prepared that contain a monosaccharide-derived sub-unit. These sugar-based crown ethers were used as chiral phase transfer catalysts in a few asymmetric reactions. A few of them proved to be effective catalysts in Michael additions, a Darzens condensation and an epoxidation of α,β-enones. It was found that the type of the monosaccharide, the substituents on the sugar unit and on the nitrogen atom of the macroring have a significant influence on both the yield and the enantioselectivity.

Original languageEnglish
Pages (from-to)51-58
Number of pages8
JournalPeriodica Polytechnica: Chemical Engineering
Volume59
Issue number1
DOIs
Publication statusPublished - 2015

Fingerprint

Crown Ethers
Crown ethers
Monosaccharides
Sugars
Macrocyclic Compounds
Catalysts
Epoxidation
Enantioselectivity
Condensation
Nitrogen
Atoms

Keywords

  • Asymmetric reactions
  • Chiral crown ethers
  • Phase transfer catalysis

ASJC Scopus subject areas

  • Chemical Engineering(all)

Cite this

Sugar-based crown ethers in enantioselective syntheses. / Bakó, P.; Rapi, Zsolt; Keglevich, G.

In: Periodica Polytechnica: Chemical Engineering, Vol. 59, No. 1, 2015, p. 51-58.

Research output: Contribution to journalArticle

@article{febd781aa74541e984cd1d9141904612,
title = "Sugar-based crown ethers in enantioselective syntheses",
abstract = "A number of chiral macrocyclic compounds have been prepared that contain a monosaccharide-derived sub-unit. These sugar-based crown ethers were used as chiral phase transfer catalysts in a few asymmetric reactions. A few of them proved to be effective catalysts in Michael additions, a Darzens condensation and an epoxidation of α,β-enones. It was found that the type of the monosaccharide, the substituents on the sugar unit and on the nitrogen atom of the macroring have a significant influence on both the yield and the enantioselectivity.",
keywords = "Asymmetric reactions, Chiral crown ethers, Phase transfer catalysis",
author = "P. Bak{\'o} and Zsolt Rapi and G. Keglevich",
year = "2015",
doi = "10.3311/PPch.7308",
language = "English",
volume = "59",
pages = "51--58",
journal = "Periodica Polytechnica: Chemical Engineering",
issn = "0324-5853",
publisher = "Budapest University of Technology and Economics",
number = "1",

}

TY - JOUR

T1 - Sugar-based crown ethers in enantioselective syntheses

AU - Bakó, P.

AU - Rapi, Zsolt

AU - Keglevich, G.

PY - 2015

Y1 - 2015

N2 - A number of chiral macrocyclic compounds have been prepared that contain a monosaccharide-derived sub-unit. These sugar-based crown ethers were used as chiral phase transfer catalysts in a few asymmetric reactions. A few of them proved to be effective catalysts in Michael additions, a Darzens condensation and an epoxidation of α,β-enones. It was found that the type of the monosaccharide, the substituents on the sugar unit and on the nitrogen atom of the macroring have a significant influence on both the yield and the enantioselectivity.

AB - A number of chiral macrocyclic compounds have been prepared that contain a monosaccharide-derived sub-unit. These sugar-based crown ethers were used as chiral phase transfer catalysts in a few asymmetric reactions. A few of them proved to be effective catalysts in Michael additions, a Darzens condensation and an epoxidation of α,β-enones. It was found that the type of the monosaccharide, the substituents on the sugar unit and on the nitrogen atom of the macroring have a significant influence on both the yield and the enantioselectivity.

KW - Asymmetric reactions

KW - Chiral crown ethers

KW - Phase transfer catalysis

UR - http://www.scopus.com/inward/record.url?scp=84922295417&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84922295417&partnerID=8YFLogxK

U2 - 10.3311/PPch.7308

DO - 10.3311/PPch.7308

M3 - Article

AN - SCOPUS:84922295417

VL - 59

SP - 51

EP - 58

JO - Periodica Polytechnica: Chemical Engineering

JF - Periodica Polytechnica: Chemical Engineering

SN - 0324-5853

IS - 1

ER -