Asymmetric Synthesis of cis- and trans-2,5-Disubstituted Pyrrolidines from 3-Oxo Pyrrolidine 2-Phosphonates: Synthesis of (+)-Preussin and Analogs

Pyrrolidine enones, derived from 3-oxo pyrrolidine 2-phosphonates and a HWE reaction with aldehydes, on Luche reduction give pyrrolidine allylic alcohols. The alcohols on hydrogenation (Pd/H2) give cis-2,5-disubstituted pyrrolidines and on treatment with TFA-NaBH3CN undergo a hydroxy directed reduction to trans-2,5-disubstituted pyrrolidines.