Synthetic Aromatic Amino Acids from a Negishi Cross-Coupling Reaction

Abstract

An N,O-protected, iodinated bishomoalanine derivative, safely available from glutamic acid, reacts with aryl halides in a Negishi reaction in high yields. From the coupling product, Fmoc-protected amino acids with aromatic and heteroaromatic side chains were generated in high yields by racemization-free procedures. These monomers could be used for solid-phase peptide synthesis.

Key words

amino alcohols - chiral pool - nickel catalyst - RNA ligand - zinc organyls

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15

Due to the observed dynamic effects for the oxazolidine systems 4, 5, 7a-g, 16-18 an exact assignment was not possible. The existence of dynamic effects was exemplarily shown by a high temperature ^¹H NMR spectrum of compound 7a.