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Storch G, Haas M, Trapp O. Attracting Enantiomers: Chiral Analytes That Are Simultaneously Shift Reagents Allow Rapid Screening of Enantiomeric Ratios by NMR Spectroscopy. Chemistry. 2017;23(23):5414-5418doi: 10.1002/chem.201700461.
Storch, G., Haas, M., & Trapp, O. (2017). Attracting Enantiomers: Chiral Analytes That Are Simultaneously Shift Reagents Allow Rapid Screening of Enantiomeric Ratios by NMR Spectroscopy. Chemistry (Weinheim an der Bergstrasse, Germany), 23(23), 5414-5418. https://doi.org/10.1002/chem.201700461
Storch, Golo, et al. "Attracting Enantiomers: Chiral Analytes That Are Simultaneously Shift Reagents Allow Rapid Screening of Enantiomeric Ratios by NMR Spectroscopy." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,23 (2017): 5414-5418. doi: https://doi.org/10.1002/chem.201700461
Storch G, Haas M, Trapp O. Attracting Enantiomers: Chiral Analytes That Are Simultaneously Shift Reagents Allow Rapid Screening of Enantiomeric Ratios by NMR Spectroscopy. Chemistry. 2017 Apr 24;23(23):5414-5418. doi: 10.1002/chem.201700461. Epub 2017 Apr 03. PMID: 28317203.
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Chemistry. 2017 Apr 24;23(23):5414-5418. doi: 10.1002/chem.201700461. Epub 2017 Apr 03.

Attracting Enantiomers: Chiral Analytes That Are Simultaneously Shift Reagents Allow Rapid Screening of Enantiomeric Ratios by NMR Spectroscopy.

Chemistry (Weinheim an der Bergstrasse, Germany)

Golo Storch, Maren Haas, Oliver Trapp

Affiliations

  1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, München, Germany.
  2. Max-Planck-Institute for Astronomy, Königstuhl 17, 69117, Heidelberg, Germany.

PMID: 28317203 DOI: 10.1002/chem.201700461

Abstract

The rapid and direct determination of enantiomeric ratios is of increasing interest due to the significantly reduced effort compared to chromatographic methods and the large number of analytes, for instance in enantioselective catalysis. Current strategies include colorimetric assays, (a)chiral solvating reagents for NMR spectroscopy and metal complexes for CD sensing. We report the determination of enantiomeric ratios based on the self-induced diastereomeric anisochronism (SIDA) effect. Alanine derivatives that represent chiral products of enantioselective catalysis, such as the well-established hydrogenation of dehydroamino acids, were investigated. The SIDA effect was significantly enhanced by attachment of 3,5-dinitrobenzoyl π-π interactions sites. This simple modification enabled simultaneous determination of enantiomeric ratios and conversions by NMR spectroscopy.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: NMR spectroscopy; amino acids; e.r. determination; non-covalent interactions; supramolecular chemistry

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