Synthesis and Resolution of an Axially Chiral Spirocyclic Quaternary Ammonium Ion-Based Phase-Transfer Catalyst

We report the synthesis of a novel spirocyclic quaternary ammonium salt that possesses axial chirality. Enantiopure material was obtained by fractional crystallization of the corresponding (R,R)-tartrate salt. Application of this chiral quaternary ammonium salt in phase-transfer catalytic asymmetric alkylation of glycinate Schiff base was examined.

Automated summary

We have synthesized a new spirocyclic quaternary ammonium salt with axial chirality. Enantiopure material was achieved through fractional crystallization of the corresponding (R, R)-tartrate salt. The application of this chiral quaternary ammonium salt in phase-transfer catalytic asymmetric alkylation of glycinate Schiff base was investigated.