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 inOrganic letters Vol. 26; no. 20; pp. 4262 - 4267
Main Authors Zhang, Zhou, Liang, Fei-Fei, Zhang, Shu-Lin, Sun, Wei, Zhou, An-Xi, Sun, Meng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.05.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ENANTIOSELECTIVE SYNTHESIS
3+2 CYCLOADDITION
ACCESS
SESQUITERPENE LACTONES
WATER
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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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c01200