An insight into the synthesis of novel aryl-substituted alicyclic β-amino acid derivatives through substrate-directed palladium-catalysed regio- and stereoselective cross-coupling

Melinda Nonn, L. Kiss, Mikko M. Hänninen, F. Fülöp

Research output: Contribution to journalArticle

Abstract

Novel aryl-substituted alicyclic β-amino acid derivatives were synthesized through substrate-determined palladium-catalysed cross-coupling of aryl iodides with five- or six-membered cycloalkene β-amino esters. The arylations were investigated with different catalysts, solvents, bases and aryl halides, and with some cyclohexene 2-aminocarboxylate isomers. The stereochemistry and the position of the ring olefinic bond of the starting 2-aminocycloalkanecarboxylate influenced the coupling reaction, and predetermined the structure of the arylated product. This journal is

Original languageEnglish
Pages (from-to)13628-13634
Number of pages7
JournalRSC Advances
Volume5
Issue number18
DOIs
Publication statusPublished - 2015

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Cycloparaffins
Stereochemistry
Palladium
Iodides
Isomers
Amino acids
Esters
Derivatives
Amino Acids
Catalysts
Substrates
cyclohexene

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

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AU - Nonn, Melinda

AU - Kiss, L.

AU - Hänninen, Mikko M.

AU - Fülöp, F.

PY - 2015

Y1 - 2015

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AB - Novel aryl-substituted alicyclic β-amino acid derivatives were synthesized through substrate-determined palladium-catalysed cross-coupling of aryl iodides with five- or six-membered cycloalkene β-amino esters. The arylations were investigated with different catalysts, solvents, bases and aryl halides, and with some cyclohexene 2-aminocarboxylate isomers. The stereochemistry and the position of the ring olefinic bond of the starting 2-aminocycloalkanecarboxylate influenced the coupling reaction, and predetermined the structure of the arylated product. This journal is

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