6533b834fe1ef96bd129ce92

RESEARCH PRODUCT

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

Loránd KissMikko M. HänninenFerenc FülöpFerenc FülöpMelinda NonnMelinda Nonn

subject

chemistry.chemical_classificationsynthesisGeneral Chemical EngineeringArylCyclohexenechemistry.chemical_elementGeneral ChemistryRing (chemistry)Medicinal chemistryCoupling reactionCatalysischemistry.chemical_compoundAlicyclic compoundchemistrycross-couplingOrganic chemistryta116CycloalkenePalladium

description

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.

https://doi.org/10.1039/c4ra16196c