H. Deboves, C. Montalbetti, R. Jackson
2001
Citations
0
Influential Citations
27
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The new N-Fmoc 3-iodoalanine tert-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 tert-butyl group gives Fmoc-protected amino acids (63–95%), suitable for use in automated solid phase peptide synthesis.