Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives
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2024
Authors
Jovanović, PredragJovanović, Miloš
Petković, Miloš
Simić, Milena
Tasić, Gordana
Rodić, Marko
Rakić, Srđan
Vlahović, Filip
Savić, Vladimir
Article (Published version)
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Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane-type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd-catalysis, affording π-allyl Pd-species, was followed by two additional transformations - nucleophilic displacement and dipolar cycloaddition - to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT.
Keywords:
allenes / cascade reactions / cycloaddition reactions / DFT / oximes / palladium catalysisSource:
Advanced Synthesis and Catalysis, 2024Publisher:
- John Wiley and Sons Inc
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200161 (University of Belgrade, Faculty of Pharmacy) (RS-MESTD-inst-2020-200161)
DOI: 10.1002/adsc.202400253
ISSN: 1615-4150
WoS: 001270707000001
Scopus: 2-s2.0-85198754718
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IHTMTY - JOUR AU - Jovanović, Predrag AU - Jovanović, Miloš AU - Petković, Miloš AU - Simić, Milena AU - Tasić, Gordana AU - Rodić, Marko AU - Rakić, Srđan AU - Vlahović, Filip AU - Savić, Vladimir PY - 2024 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/7800 AB - Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane-type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd-catalysis, affording π-allyl Pd-species, was followed by two additional transformations - nucleophilic displacement and dipolar cycloaddition - to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT. PB - John Wiley and Sons Inc T2 - Advanced Synthesis and Catalysis T1 - Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives DO - 10.1002/adsc.202400253 ER -
@article{ author = "Jovanović, Predrag and Jovanović, Miloš and Petković, Miloš and Simić, Milena and Tasić, Gordana and Rodić, Marko and Rakić, Srđan and Vlahović, Filip and Savić, Vladimir", year = "2024", abstract = "Combining chemical reactivities of allenes and oximes created a methodology for the preparation of heterocyclic triquinane-type skeletons via a cascade process constructing four bonds in a single step. The initial reaction of allene moiety promoted by Pd-catalysis, affording π-allyl Pd-species, was followed by two additional transformations - nucleophilic displacement and dipolar cycloaddition - to furnish the product highly stereoselectively in moderate to good yields. For the process to be efficient, it was necessary to use a dipolarophilic component as a solvent. Intriguingly, while the reaction with cyclopentanone derived oxime progressed through the whole cascade, with cyclohexanone analogue it stopped at the nitrone stage, requiring an additional step to yield similar type of products. Some aspects of the studied cascade were examined by DFT.", publisher = "John Wiley and Sons Inc", journal = "Advanced Synthesis and Catalysis", title = "Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives", doi = "10.1002/adsc.202400253" }
Jovanović, P., Jovanović, M., Petković, M., Simić, M., Tasić, G., Rodić, M., Rakić, S., Vlahović, F.,& Savić, V.. (2024). Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives. in Advanced Synthesis and Catalysis John Wiley and Sons Inc.. https://doi.org/10.1002/adsc.202400253
Jovanović P, Jovanović M, Petković M, Simić M, Tasić G, Rodić M, Rakić S, Vlahović F, Savić V. Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives. in Advanced Synthesis and Catalysis. 2024;. doi:10.1002/adsc.202400253 .
Jovanović, Predrag, Jovanović, Miloš, Petković, Miloš, Simić, Milena, Tasić, Gordana, Rodić, Marko, Rakić, Srđan, Vlahović, Filip, Savić, Vladimir, "Three Component Cascade Processes Involving Palladium Catalyzed Transformations/Dipolar Cycloadditions for the Synthesis of Angular Heterotriquinane Derivatives" in Advanced Synthesis and Catalysis (2024), https://doi.org/10.1002/adsc.202400253 . .