308807-17-2Relevant articles and documents
A new route to hydrophobic amino acids using copper-promoted reactions of serine-derived organozinc reagents
Deboves, Herve J.C.,Grabowska, Urszula,Rizzo, Adriana,Jackson, Richard F.W.
, p. 4284 - 4292 (2000)
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.