Work

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

Year: 2026

Type: article

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.

Source: Chemical Science

DOI: 10.1039/d6sc05947c

Authors: Maximilian Iglhaut, Biki Ghosh, Thorsten Bach

Institution: Technical University of Munich

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Alexander von Humboldt-Stiftung, European Commission, European Research Council

Award: G2021787237