IR spectroscopy as a high-throughput screening-technique for enantioselective hydrogen-transfer catalysts

Petra, Daniëlle G. I.; Reek, Joost N. H.; Kamer, Paul C. J.; Leeuwen, Piet W. N. M. van

doi:10.1039/b000479k

Cited by 27 publications

(10 citation statements)

References 15 publications

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“…To date, a number of techniques are under development for the high-throughput enantiomeric composition determination [13][14][15][16][17], including time resolved IR-thermographic method [18][19][20][21], electron spray mass spectrometry [22][23][24][25][26], capillary electrophoresis [27], UV/Vis [28][29][30], circular dichroism [31,32], and fluorescence [33,34]. Among these approaches, optical methods have been attracting increasing attention due to their ability for quick data collection and compatibility with high-throughput screening system.…”

Section: Advances In Chemistrymentioning

confidence: 99%

Chiral Recognition by Fluorescence: One Measurement for Two Parameters

Sheng

2014

Advances in Chemistry

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This outlook describes two strategies to simultaneously determine the enantiomeric composition and concentration of a chiral substrate by a single fluorescent measurement. One strategy utilizes a pseudoenantiomeric sensor pair that is composed of a 1,1 -bi-2-naphthol-based amino alcohol and a partially hydrogenated 1,1 -bi-2-naphthol-based amino alcohol. These two molecules have the opposite chiral configuration with fluorescent enhancement at two different emitting wavelengths when treated with the enantiomers of mandelic acid. Using the sum and difference of the fluorescent intensity at the two wavelengths allows simultaneous determination of both concentration and enantiomeric composition of the chiral acid. The other strategy employs a 1,1 -bi-2-naphthol-based trifluoromethyl ketone that exhibits fluorescent enhancement at two emission wavelengths upon interaction with a chiral diamine. One emission responds mostly to the concentration of the chiral diamine and the ratio of the two emissions depends on the chiral configuration of the enantiomer but independent of the concentration, allowing both the concentration and enantiomeric composition of the chiral diamine to be simultaneously determined. These strategies would significantly simplify the practical application of the enantioselective fluorescent sensors in high-throughput chiral assay.

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Section: Advances In Chemistrymentioning

confidence: 99%

Chiral Recognition by Fluorescence: One Measurement for Two Parameters

Sheng

2014

Advances in Chemistry

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“…Three years later, van Leeuwen [24] developed a new screening technique to measure the enantiomeric excess of chiral hydrogen-transfer catalysts in the reduction of acetophenone using ephedrine 27 or phenylglycinol 28 as ligands (Scheme 6). A single measurement was sufficient to calculate the enantiomeric excess of each mixture by subtracting a reference spectrum from each sample spectrum.…”

Section: Infrared Spectrometrymentioning

confidence: 99%

High Throughput Screening Methods for Asymmetric Synthesis

Charbonneau¹,

Ogilvie

2005

MROC

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“…We conclude that this method nevertheless has some potential in the determination of ee values (and other types of screening). Finally, van Leeuwen has shown that in some cases IR spectroscopy is useful in the evaluation of asymmetric reactions 95…”

Section: High‐throughput Screening Systems For Assaying Enantioselmentioning

confidence: 99%

Combinatorial and Evolution-Based Methods in the Creation of Enantioselective Catalysts

Reetz

2001

Angew. Chem. Int. Ed.

567

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Combinatorial methods in the development of enantioselective homogeneous catalysts constitute a new branch of catalysis research. The goal is to prepare libraries of potential asymmetric catalysts, rather than choosing the traditional one‐catalyst‐at‐a‐time approach. Several conceptional advancements have been reported in the parallel preparation of chiral ligands. Currently the most meaningful systems constitute modularly constructed ligands on solid supports, which allow high degrees of structural diversity and thus the maximum probability of finding enantioselective catalysts or even new types of ligands for asymmetric catalysis. Search strategies have been developed which amongst other things, lead to catalysts not likely to have been discovered by traditional methods. Genuine application of such strategies involve thousands of catalysts and require high‐throughput screening systems capable of assaying enantioselectivity. The first high‐throughput ee‐screening systems were in fact developed for use in the directed evolution of enantioselective enzymes, a process based on “evolution in the test tube” in which the appropriate methods of random mutagenesis, gene expression, and ee assays are combined. Since no screening system is likely to be universal, different approaches are necessary. Thus far these include assays based on UV/Vis, fluorescence, circular dichroism, mass spectrometry, and even modified gas chromatography as well as special forms of capillary electrophoresis. One of the most efficient systems involves the concept of the mass‐spectrometric detection of deuterium‐labeled pseudo‐enantiomers and pseudo‐prochiral compounds with which about 1000 exact ee determinations can be achieved per day, although the assay is restricted to kinetic resolution and/or reactions of prochiral compounds bearing enantiotopic groups. Super‐high‐throughput screening for enantioselectivity is possible in many cases by making use of chirally modified capillary array electrophoresis in a parallel step. Accordingly, 7000 to 30 000 ee determinations can be carried out per day. These and other analytical developments are expected to stimulate further research in the combinatorial search for asymmetric homogeneous catalysts and in the directed evolution of enantioselective enzymes for use in organic chemistry.

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IR spectroscopy as a high-throughput screening-technique for enantioselective hydrogen-transfer catalysts

Abstract: A new high-throughput screening-technique based on IR spectroscopy has been developed for ruthenium catalysed asymmetric transfer-hydrogenation by comparing the reaction rate of the reduction of ketones using (R)-vs. (S)secondary alcohol as the hydrogen donor.

Cited by 27 publications

References 15 publications

Chiral Recognition by Fluorescence: One Measurement for Two Parameters

Chiral Recognition by Fluorescence: One Measurement for Two Parameters

High Throughput Screening Methods for Asymmetric Synthesis

Combinatorial and Evolution-Based Methods in the Creation of Enantioselective Catalysts

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