Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures

F. Yushra Thanzeel, Kaluvu Balaraman and Christian Wolf ()
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F. Yushra Thanzeel: Georgetown University
Kaluvu Balaraman: Georgetown University
Christian Wolf: Georgetown University

Nature Communications, 2018, vol. 9, issue 1, 1-8

Abstract: Abstract Click reactions have become powerful synthetic tools with unique applications in the health and materials sciences. Despite the progress with optical sensors that exploit the principles of dynamic covalent chemistry, metal coordination or supramolecular assemblies, quantitative analysis of complex mixtures remains challenging. Herein, we report the use of a readily available coumarin conjugate acceptor for chiroptical click chirality sensing of the absolute configuration, concentration and enantiomeric excess of several compound classes. This method has several attractive features, including wide scope, fast substrate fixation without by-product formation or complicate equilibria often encountered in reversible substrate binding, excellent solvent compatibility, and tolerance of air and water. The ruggedness and practicality of this approach are demonstrated by comprehensive analysis of nonracemic monoamine samples and crude asymmetric imine hydrogenation mixtures without work-up. Click chemosensing addresses increasingly important time efficiency, cost, labor and chemical sustainability aspects and streamlines asymmetric reaction development at the mg scale.

Date: 2018
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DOI: 10.1038/s41467-018-07695-9

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