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Synfacts 2024; 20(06): 0631
DOI: 10.1055/s-0043-1774837
Organo- and Biocatalysis

Cooperative Photoredox and Chiral Brønsted Acid Catalysis Permits Asymmetric [2π+2σ] Cycloaddition

Contributor(s):
Benjamin List
,
Wencke Leinung
Fu Q, Cao S, Wang J, *, Lv X, *, Wang H, Zhao X, Jiang Z. * Henan Normal University, Xinxiang and Henan University, Kaifeng, P. R. of China
Enantioselective [2π + 2σ] Cycloadditions of Bicyclo[1.1.0]butanes with Vinylazaarenes through Asymmetric Photoredox Catalysis.

J. Am. Chem. Soc. 2024;
146: 8372-8380
DOI: 10.1021/jacs.3c14077
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Key words

asymmetric photoredox catalysis - Brønsted acid catalysis - [2π+2σ] cycloaddition - bicyclobutanes

Significance

Wang, Lv, Jiang, and co-workers disclosed an asymmetric photoredox and Brønsted acid-catalyzed [2π+2σ] cycloaddition of bicyclobutanes and vinyl azaarenes. The chiral cycloadducts are furnished in mostly moderate to very good yields with good to excellent enantioselctivity.


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Comment

Introducing 10-phenylanthracen-9-yl substituents into the chiral phosphoric acid transforms the catalyst into a bifunctional entity, both capable of providing a chiral environment and serving as a photosensitizer for the cycloaddition. We highly anticipate an experimental validation of the proposed water-assisted radical addition step.


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Publication History

Article published online:
14 May 2024

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