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Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry (CROSBI ID 309647)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Hilgers, Roelant ; Teng, Sin Yong ; Briš, Anamarija ; Pereverzev, Aleksandr Y. ; White, Paul ; Jansen, Jeroen ; Roithová, Jana Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry // Angewandte Chemie. International edition, 2022 (2022), e202205720, 15. doi: 10.1002/anie.202205720

Podaci o odgovornosti

Hilgers, Roelant ; Teng, Sin Yong ; Briš, Anamarija ; Pereverzev, Aleksandr Y. ; White, Paul ; Jansen, Jeroen ; Roithová, Jana

engleski

Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry

Enantioselective reactions are at the core of chemical synthesis. Their development mostly relies on prior knowledge, laborious product analysis and post-rationalization by theoretical methods. Here, we introduce a simple and fast method to determine enantioselectivities based on mass spectrometry. The method is based on ion mobility separation of diastereomeric intermediates, formed from a chiral catalyst and prochiral reactants, and delayed reactant labeling experiments to link the mass spectra with the reaction kinetics in solution. The data provide rate constants along the reaction paths for the individual diastereomeric intermediates, revealing the origins of enantioselectivity. Using the derived kinetics, the enantioselectivity of the overall reaction can be predicted. Hence, this method can offer a rapid discovery and optimization of enantioselective reactions in the future. We illustrate the method for the addition of cyclopentadiene (CP) to an α, β-unsaturated aldehyde catalyzed by a diarylprolinol silyl ether.

asymmetric catalysis ; ion mobility mass spectrometry ; kinetics ; organocatalysis ; reactive intermediates

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Podaci o izdanju

2022

2022.

e202205720

15

objavljeno

1433-7851

1521-3773

10.1002/anie.202205720

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