Chiral Iminoesters Derived from d‑Glyceraldehyde in [3 + 2] Cycloaddition Reactions. Asymmetric Synthesis of a Key Intermediate in the Synthesis of Neuramidinase Inhibitors

Silver-catalyzed endo-selective and copper-catalyzed exo-selective asymmetric
[3 + 2] cycloadditions of acrylates
to chiral iminoesters derived from d-glyceraldehyde have
been investigated. The reaction diastereoselectively provides highly
functionalized pyrrolidines. This approach was used to develop the
first asymmetric synthesis of a key intermediate in the synthesis
of pyrrolidine influenza neuramidinase inhibitors.