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Lookup NU author(s): Herve Deboves,
Professor Richard Jackson
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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.
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
ISSN (print): 1472-7781
ISSN (electronic): 1364-5463
Publisher: Royal Society of Chemistry
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