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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 Kiss,Mikko M. Hänninen
RSC Advances Pub Date : 01/12/2015 00:00:00 , DOI:10.1039/C4RA16196C
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.

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