Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids

HJC Deboves, CAGN Montalbetti…

Index: Deboves; Montalbetti; Jackson Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 16 p. 1876 - 1884

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Citation Number: 31

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 ...