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

Lookup NU author(s): Herve Deboves, Professor Richard Jackson

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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. © The Royal Society of Chemistry 2000.


Publication metadata

Author(s): Deboves HJC, Grabowska U, Rizzo A, Jackson RFW

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society, Perkin Transactions 1

Year: 2000

Issue: 24

Pages: 4284-4292

ISSN (print): 1472-7781

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b007032g

DOI: 10.1039/b007032g


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