To our surprise, the proposed cascade also allowed us to access both cis and trans pyrrolidines in good to excellent diastereo and enantioselectivities, dependent on the biocatalyst utilized. These results show that some IREDs retain absolute enantiopreference in both steps, affording trans products (e.g. 2S,5S-21i from IR23), while others switch selectivity to afford the cis products (e.g. 2S,5R-21i from IR49). These findings indicate that the -substrate binding modes differ broadly among the evaluated IREDs and the acyclic/cyclic imine intermediates. Furthermore, the access to both diastereoisomers suggests that the diastereoselectivity is primarily governed by the enzyme and not chemically dictated by the previously defined stereocenter.