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DOI: 10.1055/a-2601-4255
Photocatalyst-Dependent Deracemization of Cyclic α-Aryl Ketones via ACPC
Photocatalyst-Dependent Enantioselectivity in the Light-Driven Deracemization of Cyclic α-Aryl Ketones.
J. Am. Chem. Soc. 2025;
147: 15307-15317
DOI: 10.1021/jacs.5c00847
Keywords
enantiocontrol - photocatalytic - asymmetric catalysis - deracemization - α-aryl ketones - redox properties
Significance
This study describes an asymmetric counteranion directed photoredox catalysis (ACPC)-enabled deracemization of cyclic α-aryl ketones that occurs through mechanistically distinct proton transfer processes and has excellent stereoselectivity and yield. The extent of deracemization of this reaction shows an unexpected dependence on the concentration of a chiral base cocatalyst and the identity of the photocatalyst. Increasing the concentration of the chiral base cocatalyst, using photocatalysts with more positive ground-state reduction potentials, or a combination of these factors, can increase the degree of deracemization.
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Comment
Using light-driven deracemization processes, appropriate racemic or scalemic mixtures can be converted into enantioenriched products. To accomplish a high level of deracemization with higher yield, this technique uses a visible-light photocatalyst in conjunction with a chiral phosphate counteranion. The photomediated synthesis of chiral natural compounds can benefit from the instructions provided by this work.
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Publication History
Article published online:
23 June 2025
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