Abstract
Molecular recognition, activation and dynamic self-assembly with Brønsted and Lewis acids play a central role across the chemical sciences including catalysis, crystal engineering, supramolecular architectures and drug design. Despite this general advance, the utilization of the corresponding binding motifs for fast and robust quantitative chemosensing of chiral compounds in a complicate matrix has remained challenging. Here we show that a stereodynamic probe carrying complementary boronic acid and urea units achieves this goal with hydroxy carboxylic acids. Synergistic dual-site binding and instantaneous chirality imprinting result in characteristic ultraviolet and CD readouts that allow instantaneous determination of the absolute configuration, enantiomeric excess and concentration of the target compound even in complex mixtures. The robustness and practicality of this strategy for high-throughput screening purposes is demonstrated. Comprehensive sensing of only 0.5 mg of a crude reaction mixture of an asymmetric reduction eliminates cumbersome work-up protocols and minimizes analysis time, labour and waste production.
Highlights
Molecular recognition, activation and dynamic self-assembly with Brønsted and Lewis acids play a central role across the chemical sciences including catalysis, crystal engineering, supramolecular architectures and drug design
This remaining bottleneck has pointed increasing attention to fast chromatographic methods[5], mass spectrometry[6,7,8], fluorescence[9,10,11] and ultraviolet (UV)[12,13] spectroscopy, infrared (IR) thermography[14], NMR spectroscopy[15,16], electrochemistry[17], and biochemical assays[18,19,20], all of which share the potential for high-throughput screening (HTS) of asymmetric reactions
The broad usefulness of the urea unit in asymmetric organocatalysis and crystal engineering applications originates from its ability to participate in directional hydrogen bonding to carboxylate and other functionalities[42,43]
Summary
Activation and dynamic self-assembly with Brønsted and Lewis acids play a central role across the chemical sciences including catalysis, crystal engineering, supramolecular architectures and drug design. The general utility and ruggedness of this approach is demonstrated by analysis of the yield, ee and sense of asymmetric induction of crude reaction mixtures obtained by Ipc2BCl reductions of an a-keto acid.
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