Comparison of a molecular and an immobilized gadolinium(III)-tris[(1R,4S)-3-heptafluorobutanoyl-camphor] as catalyst in the asymmetric Danishefsky-hetero-Diels-Alder-reaction
On-column reaction gas chromatography combines the power of separation and rapid analysis of reactants and reaction products with screening of reactions in a single step. Not only conversions but the reaction rates at various temperatures can be obtained from single measurements, making this approac...
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| Main Authors: | , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
19 March 2014
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| In: |
Chirality
Year: 2014, Volume: 26, Issue: 4, Pages: 243-248 |
| ISSN: | 1520-636X |
| DOI: | 10.1002/chir.22312 |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/chir.22312 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chir.22312 
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| Author Notes: | Skrollan Stockinger, and Oliver Trapp |
MARC
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| 245 | 1 | 0 | |a Comparison of a molecular and an immobilized gadolinium(III)-tris[(1R,4S)-3-heptafluorobutanoyl-camphor] as catalyst in the asymmetric Danishefsky-hetero-Diels-Alder-reaction |c Skrollan Stockinger, and Oliver Trapp |
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| 520 | |a On-column reaction gas chromatography combines the power of separation and rapid analysis of reactants and reaction products with screening of reactions in a single step. Not only conversions but the reaction rates at various temperatures can be obtained from single measurements, making this approach superior to the time-consuming measurements typically performed in reaction progress analysis. However, this approach has only been used in the investigation of interconversion processes, rearrangement reactions, and only a few examples of higher-order reactions are known. Here we present the screening of immobilized gadolinium(III)-tris[(1R,4S)-3-heptafluorobutanoyl-camphor] in the Danishefsky-hetero-Diels-Alder-reaction by enantioselective on-column reaction gas chromatography utilizing cryogenic focusing to achieve catalytic conversions in this higher-order reaction and subsequent separation of the enantiomeric product mixture to determine the enantiomeric ratio. The results obtained by this approach could be transferred to the conventional batch reaction at a larger scale, demonstrating that on-column reaction chromatography provides reliable results in the screening of enantioselective reactions. Chirality 26:243-248, 2014. © 2014 Wiley Periodicals, Inc. | ||
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