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Enantioselective synthesis of heterocyclic compounds using photochemical reactions

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Abstract

Different methods for the direct enantioselective photochemical synthesis of heterocycles are presented. Currently, asymmetric catalysis with templates involving hydrogen bonds or metal complexes is intensively investigated. Enzyme catalysis can be simplified under photochemical conditions. For example, in multi enzyme systems, one or more enzyme catalytic steps can be replaced by simple photochemical reactions. Chiral induction in photochemical reactions performed with homochiral crystals is highly efficient. Such reactions can also be carried out with crystalline inclusion complexes. Inclusion of a photochemical substrate and an enantiopure compound in zeolites also leads to enantioselective compounds. In all these methods, the conformational mobility of the photochemical substrates is reduced or controlled. Memory of chirality is a particular case in which a chiral information is temporally lost but the rigid conformations stabilize the molecular structure which leads to the formation of enantiopure compounds. Such studies allows a profound understanding on how particular conformations determine the configuration of the final products.

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Acknowledgements

We are grateful for current funding of our research by the ANR (Agence nationale de la recherche, projects: IMPHOCHEM, NoPerox), the Communauté Urbaine du Grand Reims and the Université de Reims Champagne-Ardenne.

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    Norbert Hoffmann

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Hoffmann, N. Enantioselective synthesis of heterocyclic compounds using photochemical reactions. Photochem Photobiol Sci 20, 1657–1674 (2021). https://doi.org/10.1007/s43630-021-00135-6

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