A New N-Spiro C₂-Symmetric Chiral Quaternary Ammonium Bromide Consisting of 4,6-Disubstituted Biphenyl Subunit as an Efficient Chiral Phase-Transfer Catalyst

Abstract

A new N-spiro chiral quaternary ammonium bromide has been designed and assembled from optically active 4,6-disubstitute­d biphenyl subunits. Its utility as an efficient chiral phase-transfer catalyst has been clearly demonstrated by application to the highly enantioselective alkylation of tert-butyl glycinate benzophenon­e Schiff base.

chiral quaternary ammonium bromide - biphenyl subunit - glycine ester Schiff base - alkylation - α-amino acids

References

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6

Spectroscopic Characterization of 1b: [α]_D ²² +156.2 (c 0.31, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 7.37 (4 H, m, Ar-H), 7.21-7.32 (16 H, m, Ar-H), 7.14-7.19 (4 H, m, Ar-H), 7.04 (4 H, br d, J = 1.6 Hz, Ar-H), 3.87 (4 H, d, J = 13.2 Hz, ArCH₂), 3.64 (4 H, d, J = 13.2 Hz, ArCH₂), 2.18 (12 H, s, ArCH₃), 1.68 (24 H, s, ArCCH₃). ¹³C NMR (100 MHz, CDCl₃): δ = 150.8, 149.7, 137.5, 135.5, 131.2, 128.2, 127.5, 126.7, 126.5, 125.8, 60.3, 42.9, 31.0, 30.5, 20.2. IR (KBr): 2963, 2928, 2870, 1740, 1680, 1601, 1495, 1445, 1383, 1364, 1232, 1202, 1097, 1076, 1030, 845, 768, 702 cm^-1. HRMS (ESI-TOF): Calcd for C₆₈H₇₂N: 902.5659 (M⁺). Found: 902.5673 (M⁺).