ArticleAngewandte Chemie (International ed. in English)2022
Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 17 citations in OpenAlex.
- Mechanistic insights into nonlinear effects in copper-catalyzed asymmetric esterification.Nature communications · 2025Article
- Generation, Spectroscopic Characterization, and Computational Analysis of a Six-Coordinate Cobalt(III)-Imidyl Complex with an UnusualJournal of the American Chemical Society · 2023Article
- Kinetics of ligand exchange in solution: a quantitative mass spectrometry approach.Chemical science · 2023Article
- Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
7 authors at 1 institution in 1 country.
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Abstract
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.
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