Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation

A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C–C bond activation and intermolecular allylic substitution was well-organized. The key for this transformati...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (20), p.4262-4267
Main Authors: Zhang, Zhou, Liang, Fei-Fei, Zhang, Shu-Lin, Sun, Wei, Zhou, An-Xi, Sun, Meng
Format: Article
Language:English
Subjects:
allylation
cinnamates
hydrolysis
reaction mechanisms
stereoselective synthesis
stereoselectivity
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Summary:A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process of C–C bond activation and intermolecular allylic substitution was well-organized. The key for this transformation is the in situ generated hydrolysis product of cyclopropenone, which triggered a new reaction with vinylethylene carbonates. The reaction mechanism was investigated, demonstrating the high stereoselectivity and excellent atomic economy in this process.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01200