Diastereo- and Enantioselective Synthesis of Pyrrolidines

Significance

Functionalized pyrrolidines have drawn much interest due to the bioactive properties seen in natural and unnatural products bearing this moiety. As such, there is an important need for asymmetric methods for the synthesis of these structural motifs. The authors disclose a gold(I)-catalyzed diastereo- and enantioselective method for the synthesis of 3,4-substituted pyrrolidines and γ-lactones. Yields range from moderate to excellent, and enantioselectivities are generally good for the reported examples. A DFT study is performed to gain mechanistic insight into the methodology and the formal synthesis of (-)-isocyanometrine is undertaken to demonstrate the synthetic utility of the reaction.