Chemodiscrimination of Olefin Bonds Through Cross-Metathesis Reactions – Synthesis of Functionalized β-Lactam and β-Amino Acid Derivatives

Melinda Nonn, Zsanett Benke, Santos Fustero, F. Fülöp, L. Kiss

Research output: Article

Abstract

Chemodifferentiation of C=C bonds of various diolefinated β-lactams or β-amino esters has been investigated through cross-metathesis reactions. The transformations involved substrate-dependent cross-metathesis of dialkenylated azetidinones, derived from the ring opening of constrained unsaturated bicyclic β-lactam isomers. Cross-metathesis reactions have been carried out under various conditions and catalysts in view of chemodiscrimination affording functionalized β-lactams or β-amino acid derivatives.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusPublished - jan. 1 2019

Fingerprint

Lactams
metathesis
Alkenes
alkenes
amino acids
Derivatives
Amino Acids
synthesis
Isomers
esters
Esters
isomers
catalysts
Catalysts
rings
Substrates

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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title = "Chemodiscrimination of Olefin Bonds Through Cross-Metathesis Reactions – Synthesis of Functionalized β-Lactam and β-Amino Acid Derivatives",
abstract = "Chemodifferentiation of C=C bonds of various diolefinated β-lactams or β-amino esters has been investigated through cross-metathesis reactions. The transformations involved substrate-dependent cross-metathesis of dialkenylated azetidinones, derived from the ring opening of constrained unsaturated bicyclic β-lactam isomers. Cross-metathesis reactions have been carried out under various conditions and catalysts in view of chemodiscrimination affording functionalized β-lactams or β-amino acid derivatives.",
keywords = "Amino acids, Chemoselectivity, Lactams, Metathesis, Stereocontrol",
author = "Melinda Nonn and Zsanett Benke and Santos Fustero and F. F{\"u}l{\"o}p and L. Kiss",
year = "2019",
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journal = "Annalen der Pharmacie",
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T1 - Chemodiscrimination of Olefin Bonds Through Cross-Metathesis Reactions – Synthesis of Functionalized β-Lactam and β-Amino Acid Derivatives

AU - Nonn, Melinda

AU - Benke, Zsanett

AU - Fustero, Santos

AU - Fülöp, F.

AU - Kiss, L.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Chemodifferentiation of C=C bonds of various diolefinated β-lactams or β-amino esters has been investigated through cross-metathesis reactions. The transformations involved substrate-dependent cross-metathesis of dialkenylated azetidinones, derived from the ring opening of constrained unsaturated bicyclic β-lactam isomers. Cross-metathesis reactions have been carried out under various conditions and catalysts in view of chemodiscrimination affording functionalized β-lactams or β-amino acid derivatives.

AB - Chemodifferentiation of C=C bonds of various diolefinated β-lactams or β-amino esters has been investigated through cross-metathesis reactions. The transformations involved substrate-dependent cross-metathesis of dialkenylated azetidinones, derived from the ring opening of constrained unsaturated bicyclic β-lactam isomers. Cross-metathesis reactions have been carried out under various conditions and catalysts in view of chemodiscrimination affording functionalized β-lactams or β-amino acid derivatives.

KW - Amino acids

KW - Chemoselectivity

KW - Lactams

KW - Metathesis

KW - Stereocontrol

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