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Peer-reviewedCC BY 3.0Chemical Science

Photochemical deracemization of α-chiral carboxamides mediated by inter- and intramolecular hydrogen bonding

  • Maximilian Iglhaut1
  • Biki Ghosh1
  • Thorsten Bach1
  1. 1Technische Universität München, School of Natural Sciences, Department of Chemistry and Catalysis Research Center Lichtenbergstrasse 4 85747 Garching Germany https://www.ch.nat.tum.de/en/oc1/home/
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Abstract

Photochemical deracemization allows for the direct generation of enantiomerically pure or enriched compounds from their racemates employing a single chiral catalyst. In the present study, carboxylic acid amides (carboxamides) with a substituent in the α-position were investigated in a photochemical deracemization mediated by a chiral aromatic ketone. The catalyst displays a hydrogen bonding site which allows for a differentiation between the two enantiomers and operates by a reversible hydrogen atom transfer. It was found that α-alkoxy or α-amino substituents enable an efficient deracemization (up to 99.5 : 0.5 e.r.) due to a second intramolecular hydrogen bonding interaction locking a distinct substrate conformation.

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Cite

BibTeXRIS
BibTeX
@article{iglhaut2026photochemical,
  title = {{Photochemical deracemization of α-chiral carboxamides mediated by inter- and intramolecular hydrogen bonding}},
  author = {Maximilian Iglhaut and Biki Ghosh and Thorsten Bach},
  journal = {Chemical Science},
  year = {2026},
  month = sep,
  doi = {10.1039/d6sc05947c},
  url = {https://doi.org/10.1039/d6sc05947c},
  note = {CC BY 3.0},
}
RIS
TY  - JOUR
TI  - Photochemical deracemization of α-chiral carboxamides mediated by inter- and intramolecular hydrogen bonding
AU  - Maximilian Iglhaut
AU  - Biki Ghosh
AU  - Thorsten Bach
PY  - 2026
DA  - 2026/09/09
JO  - Chemical Science
DO  - 10.1039/d6sc05947c
UR  - https://doi.org/10.1039/d6sc05947c
AB  - Photochemical deracemization allows for the direct generation of enantiomerically pure or enriched compounds from their racemates employing a single chiral catalyst. In the present study, carboxylic acid amides (carboxamides) with a substituent in the α-position were investigated in a photochemical deracemization mediated by a chiral aromatic ketone. The catalyst displays a hydrogen bonding site which allows for a differentiation between the two enantiomers and operates by a reversible hydrogen atom transfer. It was found that α-alkoxy or α-amino substituents enable an efficient deracemization (up to 99.5 : 0.5 e.r.) due to a second intramolecular hydrogen bonding interaction locking a distinct substrate conformation.
SN  - 2041-6520
SN  - 2041-6539
ER  -