Stereoselective Asymmetric Synthesis of Pyrrolidines with Vicinal Stereocenters Using a Memory of Chirality-Assisted Intramolecular SN2' Reaction.

An efficient strategy for the asymmetric synthesis of pyrrolidines with vicinal quaternary-tertiary or quaternary-quaternary stereocenters was established. A "memory of chirality" intramolecular SN2' reaction of α-amino ester enolates with allylic halides provided a functionalized pyrrolidine with excellent dia- and enantioselectivity. This method features construction of stereochemically enriched pyrrolidines in a single operation through the influence of a single chiral center presented in substrates.