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Free keywords:
asymmetric catalysis; phosphates; imine hydrogenation; Brønsted acids; organocatalysis
Abstract:
The chiral phosphoric acid TRIP, a useful Brønsted acid catalyst, easily becomes contaminated with metal impurities in the form of phosphate salts during synthesis. This significantly reduces the content of free acid in the product which can hamper the catalytic activity. Methods to easily judge whether TRIP contains mainly the free acid or phosphate salts are presented, using ¹H NMR spectroscopy or a simple pH test. An improved synthetic protocol for TRIP was established that reliably produces the free acid.