Stereocontrolled one-step synthesis of difunctionalised cispentacin derivatives through ring-opening metathesis of norbornene β-amino acids

L. Kiss, Márton Kardos, E. Forró, F. Fülöp

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Through the ring-opening metathesis of norbornene or oxanorbornene β-amino acids with ethylene in the presence of certain Ru catalysts, a facile and convenient stereocontrolled one-step method was devised for the preparation of divinylated cispentacins and oxacyclic cispentacin stereoisomers with four chiral centres. The products are interesting scaffolds for peptide chemistry and for the synthesis of novel functionalised materials through olefinic bond transformations. The ring-opening metathesis proceeds without affecting the chiral centres of the starting molecules, so that their stereochemistry was conserved and determines the configuration of the chiral centres in the products.

Original languageEnglish
Pages (from-to)1283-1289
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number6
DOIs
Publication statusPublished - Jan 1 2015

Fingerprint

metathesis
amino acids
Derivatives
Amino Acids
Stereochemistry
Stereoisomerism
rings
synthesis
Scaffolds
stereochemistry
products
Peptides
Catalysts
Molecules
peptides
ethylene
chemistry
catalysts
preparation
configurations

Keywords

  • Amino acids
  • Drug design
  • Enantioselective synthesis
  • Fused-ring systems
  • Medicinal chemistry
  • Metathesis
  • Peptidomimetics

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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AU - Kiss, L.

AU - Kardos, Márton

AU - Forró, E.

AU - Fülöp, F.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - Through the ring-opening metathesis of norbornene or oxanorbornene β-amino acids with ethylene in the presence of certain Ru catalysts, a facile and convenient stereocontrolled one-step method was devised for the preparation of divinylated cispentacins and oxacyclic cispentacin stereoisomers with four chiral centres. The products are interesting scaffolds for peptide chemistry and for the synthesis of novel functionalised materials through olefinic bond transformations. The ring-opening metathesis proceeds without affecting the chiral centres of the starting molecules, so that their stereochemistry was conserved and determines the configuration of the chiral centres in the products.

AB - Through the ring-opening metathesis of norbornene or oxanorbornene β-amino acids with ethylene in the presence of certain Ru catalysts, a facile and convenient stereocontrolled one-step method was devised for the preparation of divinylated cispentacins and oxacyclic cispentacin stereoisomers with four chiral centres. The products are interesting scaffolds for peptide chemistry and for the synthesis of novel functionalised materials through olefinic bond transformations. The ring-opening metathesis proceeds without affecting the chiral centres of the starting molecules, so that their stereochemistry was conserved and determines the configuration of the chiral centres in the products.

KW - Amino acids

KW - Drug design

KW - Enantioselective synthesis

KW - Fused-ring systems

KW - Medicinal chemistry

KW - Metathesis

KW - Peptidomimetics

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