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Synthesis 2010(2): 293-303  
DOI: 10.1055/s-0029-1217124
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Aromatic Amino Acids from a Negishi Cross-Coupling Reaction

Marcel Suhartono, Angelika E. Schneider, Gerd Dürner, Michael W. Göbel*
Institut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt am Main, Germany
Fax: +49(69)79829464; e-Mail: m.goebel@chemie.uni-frankfurt.de;
Further Information

Publication History

Received 26 June 2009
Publication Date:
13 November 2009 (online)

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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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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.