We recently developed a new synthetic strategy towards cis-3,4-dihydroxy-2-alkylpyrrolidines which exploits the stereodefined cyclic N,O-acetals. In the course of our efforts to extend the scope of the reaction, we recently developed a synthetic pathway towards diastereomeric trans-3,4-dihydroxy-2-alkylpyrrolidines. Notably, the protective group on the hydroxyl groups played a critical role. Application of the method in the synthesis of alkaloid natural products will be also introduced.
1. Kim, H.; Lim, W.; Im, D.; Kim, D.; Rhee, Y. H. Angew. Chem. Int., Ed. 2012, 51, 12055.