Abstract: 3-Bromo-2-fluoropropene (4) is prepared in a new three-step synthesis from ammonium α-fluoroacrylate (1) in 31% overall yield. Glycine and alanine ester imines are efficiently alkylated by 4 to give, after deprotection, 2-amino-4-fluoropent-4-enoic acid (9) in 63% overall yield, and the α-methylated derivative 13 in 26% overall yield, respectively. Preliminary results indicate that 4 is potentially a new α-carbonyl cation equivalent. Key ...
