Candida antarctica lipases acting as versatile catalysts for the synthesis of enantiopure (R)- and (S)-1-(2-phenylthiazol-4-yl)ethanamines

The synthesis of both enantiomers of four new phenylthiazole-based amines by enantiomer-selective acylation of racemic amines and by hydrolysis of the corresponding racemic amides using lipase B from Candida antarctica (Novozyme 435) as chiral catalyst was performed with good yields and excellent enantioselectivities. In order to prevent the frequently occurring partial racemization of enantiopure amides during chemical hydrolysis to the corresponding (R)-amines, the deprotection of the N-acylated (R)-enantiomers by mild enzymatic hydrolysis with lipase A from C. antarctica immobilized on Celite was also developed.