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

Abstract

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