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Synfacts 2025; 21(07): 696
DOI: 10.1055/a-2601-4426
Metals in Synthesis

Electrochemical Nickel-Catalyzed Enantioconvergent Vinylogous Radical Additions to Silyl Polyenolates

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Emilio Acuña Bolomey
Zhang J, Liu M, Zhang W, Guo C *. University of Science and Technology of China, Hefei, P. R. China
Enantioselective Electrochemical Nickel-Catalyzed Vinylogous Radical Reactions.

Sci. Adv. 2025;
11: eadu5594
DOI: 10.1126/sciadv.adu5594
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Keywords

electrochemistry - nickel catalysis - polyenes - vinylogous radical additions

Significance

Dual electrochemical and nickel catalysis enable the enantioselective vinylogous radical addition of a nickel-bound α-carboxyl radical to silyl polyenolates at the terminal position, affording enantioenriched carbonyl compounds with quaternary stereocenters at the β, δ and ζ-positions, respectively.


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Comment

Extensive cyclic voltammetry studies revealed that the ferrocene source is crucial in order to generate the nickel-bound α-keto radical. In the absence of the nickel catalyst, the direct oxidation of the ester was ruled out, preventing any racemic background reaction.


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Publication History

Article published online:
23 June 2025

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