Issue 16, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids†

Hervé J. C. Deboves,a   Christian A. G. N. Montalbettia  and  Richard F. W. Jackson*b  

* Corresponding authors

a Department of Chemistry, Bedson Building, The University of Newcastle, Newcastle upon Tyne, UK

b Department of Chemistry, Dainton Building, The University of Sheffield, Sheffield, UK

Abstract

The new N-Fmoc 3-iodoalanine tert-butyl ester derived organozinc reagent 1, obtained in 7 steps from optically pure L-serine, was coupled to a range of electrophiles under palladium catalysis to give substituted phenylalanines and 4-oxoamino acids in variable yields (21–59%). Transformation into the organocopper reagent 13 allowed coupling with allyl chloride and ethyl oxalyl chloride. Removal of the tert-butyl group gives Fmoc-protected amino acids (63–95%), suitable for use in automated solid phase peptide synthesis.

Graphical abstract: Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids

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Article information

DOI
https://doi.org/10.1039/B103832J
Article type
Paper
Submitted
27 Apr 2001
Accepted
21 Jun 2001
First published
19 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1876-1884

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Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids

H. J. C. Deboves, C. A. G. N. Montalbetti and R. F. W. Jackson, J. Chem. Soc., Perkin Trans. 1, 2001, 1876 DOI: 10.1039/B103832J

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