Coordination of a photoswitchable chiral phosphate ligand to an achiral manganese(iii)-salen complex yields a catalyst that can produce either enantiomer of an epoxide from a single alkene substrate. This enantiodivergent catalysis is governed by the transfer of the chirality of the phosphate ligand to the manganese(iii)-salen complex.
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References
Dorel, R. & Feringa, B. L. Photoswitchable catalysis based on the isomerisation of double bonds. Chem. Commun. 55, 6477–6486 (2019). A review article that presents various kinds of photoswitchable catalysts and also highlights photoswitchable enantiodivergent catalysts.
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Liao, S. & List, B. Asymmetric counteranion-directed transition-metal catalysis: enantioselective epoxidation of alkenes with manganese(III) salen phosphate complexes. Angew. Chem. Int. Ed. 49, 628–631 (2010). This paper reports the asymmetric epoxidation of alkenes using an achiral catalyst in combination with an axially chiral phosphate anionic ligand.
Pizzolato, S. F. et al. Central-to-helical-to-axial-to-central transfer of chirality with a photoresponsive catalyst. J. Am. Chem. Soc. 140, 17278–17289 (2018). This paper reports a photoresponsive catalyst that is based on the second-generation light-driven molecular motor core, and its structure resembles that of our phosphate ligand.
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This is a summary of: Chen, X. et al. Enantiodivergent epoxidation of alkenes with a photoswitchable phosphate manganese-salen complex. Nat. Synth. https://doi.org/10.1038/s44160-022-00157-7 (2022).
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A photoswitchable catalyst for the enantiodivergent epoxidation of alkenes. Nat. Synth 1, 837–838 (2022). https://doi.org/10.1038/s44160-022-00160-y
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DOI: https://doi.org/10.1038/s44160-022-00160-y
