New types of one-pot multi-step enzymatic cascade transformation involving dynamic kinetic resolution to convert racemic substrates to chiral products in high ee and yield were developed. Unique cascade reactions of easily accessible racemic trans-β-methyl or α-methyl epoxides to produce (S)-2arylpropionic acids, (R)-and (S)-2-arylpropyl amines were demonstrated via styrene oxide isomerase (SOI)catalyzed Meinwald epoxide rearrangement to generate 2-arylpropanal in situ, which was followed by spontaneous racemization, and alcohol dehydrogenase (ADH)-catalyzed (S)-enantioselective oxidation or transaminase (TA)-catalyzed (R)-or (S)-enantioselective amination, respectively. Cascade reactions performed with isolated enzymes or whole-cell biocatalysts produced pharmaceutically relevant (S)-2-arylpropionic acids, (R)-and (S)-2-arylpropyl amines with high enantioselectivity and yield. The cascades starting with in situ aldehyde generation from epoxides effectively minimized side reactions related to aldehyde instability and displayed a wide substrate scope.