4.5 Article

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

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Development of C2-Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base

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Summary: A class of C2-symmetric chiral spirocyclic phase-transfer catalysts based on the tetramethyl-1,1'-spirobiindane scaffold was synthesized in 12 steps from commercially available bisphenol A with total yields between 22-25%, featuring a more rigid and stable backbone and smaller dihedral angles that can be easily modified. These catalysts exhibit high catalytic performance in the asymmetric alkylation of tert-butyl glycinate Schiff base at only 2 mol % loading, resulting in target products with yields of up to 92% and 98% ee.

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