AI Article Synopsis
- The study introduces a new method for creating chiral β-branched ketones using readily available aldehydes through a three-component reaction involving alkenes and aryl boronic acids.
- This process features copper catalysis and relies on acyl radical formation from aldehydes via hydrogen atom transfer, leading to a series of reactions that generate valuable products.
- A specific chiral ligand, a binaphthyl-tethered bisoxazoline, is crucial for ensuring high stereocontrol in the synthesis of chiral β,β-diaryl ketones.
Article Abstract
The direct use of readily available aldehydes as acyl radical precursors has facilitated diverse three-component acylative difunctionalization reactions of alkenes, offering a powerful route to synthesize β-branched ketones. However, asymmetric three-component acylative difunctionalization of alkenes with aldehydes still remains elusive. Here we report a copper-catalyzed asymmetric three-component radical acylarylation of vinylarenes with aldehydes and aryl boronic acids. This method begins with acyl radical formation from an aldehyde via hydrogen atom transfer. The acyl radical adds to the alkene, forming a new benzylic radical that then undergoes copper-catalyzed enantioselective arylation. A chiral binaphthyl-tethered bisoxazoline ligand is essential for achieving high stereocontrol. This strategy enables the direct synthesis of a range of synthetically valuable chiral β,β-diaryl ketones from aldehydes and vinylarenes.
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| http://dx.doi.org/10.1021/jacs.4c08957 | DOI Listing |
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