Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 44, Pages 20207-20213Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c09248
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Funding
- Alexander von Humboldt Foundation
- Deutsche Forschungsgemeinschaft
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The synthesis of polysubstituted 2-oxabicyclo[2.1.1]hexanes has been achieved in a single step using visible-light-induced triplet energy transfer catalysis. This method offers significant potential in pharmaceutical development, allowing for the rapid construction of complex molecular structures and access to unexplored chemical space.
Synthesis of bicyclic scaffolds has attracted growing interest because they are of high importance in modern pharmaceutical development. Here we report a strategy to access polysubstituted 2-oxabicyclo[2.1.1]hexanes in a single operation from readily accessible benzoylformate esters and bicyclo[1.1.0]butanes via visible-light-induced triplet energy transfer catalysis. The process is proposed to involve a formal [27r + 2o-] photocycloaddition/backbone C-H abstraction/aryl group migration sequence. A diverse range of (hetero)aryl groups successfully underwent migration to the backbone (C2) position to provide previously inaccessible bicyclic molecules, and the ester group of the product can serve as a handle for downstream manipulation, thus offering opportunities to rapidly build up molecular complexity and access new sp3-rich chemical space.
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