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Synfacts 2025; 21(07): 727
DOI: 10.1055/a-2601-4930
Organo- and Biocatalysis

Asymmetric Counteranion Directed Photoredox Catalysis (ACPC)-Enabled Deracemization of Ketones

Contributor(s):
Benjamin List 
,
Ruigang Xu
Wen C, Huang Z, Zhang S-Y, Li Z, Chai B, Huang Z *, Kang Q-K *. Shanghai Institute of Organic Chemistry and Hangzhou Institute for Advanced Study, P. R. China
Deracemization of C(sp3)−H Arylated Carbonyl Compounds via Asymmetric Ion-Pairing Photoredox Catalysis.

J. Am. Chem. Soc. 2025;
147: 14625-14634
DOI: 10.1021/jacs.5c02235
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Keywords

organocatalysis - photoredox - asymmetric - deracemization - ion-pairs - ketones

Significance

Kang, Huang and co-workers report a photochemical deracemization strategy for cyclic α-aryl ketones that achieves high stereoselectivity and yield. The reaction is mediated by a cationic photocatalyst and a chiral phosphate base cocatalyst under blue light irradiation. Mechanistically, the process proceeds through distinct proton transfer pathways, enabling precise stereochemical control over the deracemization process.


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Comment

Deracemization transforms racemates into single enantiomers, offering an atom‐economical route to chiral C(sp³)–H arylated carbonyls. Traditional methods, however, are substrate‐limited and depend on stoichiometric strong bases for enolate‐mediated deprotonation/protonation sequences. The authors propose a photocatalytic approach that achieves deracemization of carbonyl compounds bearing both enolizable and non‐enolizable stereocenters under mild conditions.


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Publication History

Article published online:
23 June 2025

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