Dynamic kinetic resolution of ?-bromo carboxylic acid derivatives in nucleophilic substitution with chiral ?-amino ester nucleophiles in the presence of TBAI and DIEA has been investigated for stereoselective syntheses of 1,1'-iminodicarboxylic acid derivatives. Nucleophilic substitutions with various chiral ?-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-(?-bromo-?-phenylacetyl)-L-alanine methyl ester with L-alanine, D-alanine and glycine methyl ester nucleophiles afforded N-carboxyalkyl dipeptide analogues 10-12 up to 90 : 10 dr.