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Lookup NU author(s): Herve Deboves,
Professor Richard Jackson
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The new N-Fmoc 3-iodoalanine tort-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 tort-butyl group gives Fmoc-protected amino acids (63-95%), suitable for use in automated solid phase peptide synthesis.
Author(s): Deboves HJC, Montalbetti CAGN, 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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