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Issue 24, 2000
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A new route to hydrophobic amino acids using copper-promoted reactions of serine-derived organozinc reagents

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Abstract

Copper-catalysed reaction of the serine-derived zinc reagent 1 with allylic electrophiles gives products arising formally from both SN2 and SN2′ pathways. These constitutional isomers can be separated, either directly, or in the case of (2S )-2-tert-butoxycarbonylamino-6-methylhept-5-enoic acid methyl ester (11) and (2S )-2-tert-butoxycarbonylamino-4,4-dimethylhex-5-enoic acid methyl ester (12) by selective epoxidation of 11. Hydrogenation of the double bond, followed by protecting group manipulation, allows the synthesis of the Fmoc-protected amino acids 3–7 ready for automated peptide synthesis.

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Article information


Submitted
30 Aug 2000
Accepted
04 Oct 2000
First published
01 Dec 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 4284-4292
Article type
Paper

A new route to hydrophobic amino acids using copper-promoted reactions of serine-derived organozinc reagents

H. J. C. Deboves, U. Grabowska, A. Rizzo and R. F. W. Jackson, J. Chem. Soc., Perkin Trans. 1, 2000, 4284
DOI: 10.1039/B007032G

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