TY  - 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://farfar.pharmacy.bg.ac.rs/handle/123456789/5704
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 . .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Maslak, Veselin
AU  - Rakić, Srđan
AU  - Rodić, Marko
AU  - Vlahović, Filip
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4953
AB  - Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.
PB  - John Wiley and Sons Inc
T2  - Advanced Synthesis and Catalysis
T1  - Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis
DO  - 10.1002/adsc.202300301
ER  - 

@article{
author = "Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena and Maslak, Veselin and Rakić, Srđan and Rodić, Marko and Vlahović, Filip and Petković, Miloš and Savić, Vladimir",
year = "2023",
abstract = "Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.",
publisher = "John Wiley and Sons Inc",
journal = "Advanced Synthesis and Catalysis",
title = "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis",
doi = "10.1002/adsc.202300301"
}

Jovanović, M., Jovanović, P., Tasić, G., Simić, M., Maslak, V., Rakić, S., Rodić, M., Vlahović, F., Petković, M.,& Savić, V.. (2023). Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis
John Wiley and Sons Inc..
https://doi.org/10.1002/adsc.202300301

Jovanović M, Jovanović P, Tasić G, Simić M, Maslak V, Rakić S, Rodić M, Vlahović F, Petković M, Savić V. Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis. 2023;.
doi:10.1002/adsc.202300301 .

Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena, Maslak, Veselin, Rakić, Srđan, Rodić, Marko, Vlahović, Filip, Petković, Miloš, Savić, Vladimir, "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis" in Advanced Synthesis and Catalysis (2023),
https://doi.org/10.1002/adsc.202300301 . .