ArticleJournal of the American Chemical Society2019
Rapid Optical Determination of Enantiomeric Excess, Diastereomeric Excess, and Total Concentration Using Dynamic-Covalent Assemblies: A Demonstration Using 2-Aminocyclohexanol and Chemometrics.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 48 citations in OpenAlex.
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- A stereodynamic probe of Pt(II) molecular hinge for chiroptical sensing of cryptochiral compounds.Nature communications · 2025Article
- Chiral method validation and stereoselective degradation of profoxydim isomers in paddy soil.Environmental science and pollution research international · 2024Article
- Stimulating Chiral Selective Expression of Room Temperature Phosphorescence for Chirality Recognition.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Constitutional adaptation to pChemical science · 2024Article
- Chemometric sensing of stereoisomeric compound mixtures with a redox-responsive optical probe.Chemical science · 2024Article
- Determination of Enantiomeric Excess and Diastereomeric Excess via Optical Methods. Application to α-methyl-β-hydroxy-carboxylic acids.Organic chemistry frontiers : an international journal of organic chemistry · 2023Article
- Data-Driven Prediction of Circular Dichroism-Based Calibration Curves for the Rapid Screening of Chiral Primary Amine Enantiomeric Excess Values.Journal of the American Chemical Society · 2022Article
- Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization.Chemical reviews · 2022Review
- A Data-Driven Approach to the Development and Understanding of Chiroptical Sensors for Alcohols with Remote γ-Stereocenters.Journal of the American Chemical Society · 2021Article
- Optical deciphering of multinary chiral compound mixtures through organic reaction based chemometric chirality sensing.Nature communications · 2021Article
- High-throughput screening of α-chiral-primary amines to determine yield and enantiomeric excess.Tetrahedron · 2021Article
- Advancement in Organic Synthesis through High Throughput Experimentation.Chemistry methods : new approaches to solving problems in chemistry · 2021Article
- A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay.Angewandte Chemie (International ed. in English) · 2021Article
- Recent advances in analytical techniques for high throughput experimentation.Analytical science advances · 2021Review
- Reaction screening in multiwell plates: high-throughput optimization of a Buchwald-Hartwig amination.Nature protocols · 2021Article
- Rapid chiral analysis based on liquid-phase cyclic chemiluminescence.Chemical science · 2020Article
- Optical monitoring of polymerizations in droplets with high temporal dynamic range.Chemical science · 2020Article
- Oxidation of Sodium Deoxycholate Catalyzed by Gold Nanoparticles and Chiral Recognition Performances of Bile Salt Micelles.Molecules (Basel, Switzerland) · 2019Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Optical analysis of reaction parameters such as enantiomeric excess (ee), diastereomeric excess (de), and yield are becoming increasingly useful as assays for differing functional groups become available. These assays typically exploit reversible covalent or noncovalent assemblies that impart optical signals, commonly circular dichroism (CD), that are indicative of the stereochemistry and ee at a stereocenter proximal to the functional group of interest. Very few assays have been reported that determine ee and de when two stereocenters are present, and none have targeted two different functional groups that are vicinal and lack chromophores entirely. Using a CD assay that targets chiral secondary alcohols, a separate CD assay for chiral primary amines, a UV-vis assay for de, and a fluorescence assay for concentration, we demonstrate a work-flow for speciation of the enantiomers and diastereomers of 2-aminocyclohexanol as a test-bed analyte. Because of the fact the functional groups are vicinal, we found that the ee determination at the two stereocenters is influenced by the adjacent center, and this led us to implement a chemometric patterning approach, resulting in a 4% absolute error in full speciation of the four stereoisomers. The procedure presented herein would allow for the total speciation of around 96 reactions in 27 min using a high-throughput experimentation routine. While 2-aminocyclohexanol is used to demonstrate the methods, the general workflow should be amenable to analysis of other stereoisomers when two stereocenters are present.
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