The synthesis and transformations of 2-aminocycloalkanecarboxylic acids were discussed. The resolution of the racemates by diastereomer separation and biocatalyzed transformations were studied. It was found that the selective reductive aminations of β-ketoesters via enamines resulted into the accurate ratios of cis and trans diastereomers. The synthesis of 2-aminocycloalkanecarboxylic acids from 1,2-dicarboxylic acids derivatives by rearrangements was also elaborated.