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

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.