Stereoconvergent Synthesis of Cyclopentenyl Nucleosides by Palladium‐Assisted Allylic Reaction
Abstract: The Tsuji‐Trost reaction of cyclopentenyl carbonates was explored by experimental studies and computational calculations, in search for the synthetic conditions enabling the stereoconvergent synthesis of cyclopentenyl nucleosides. Under common conditions, cyclopentenyl reagents provide Tsuji‐Trost products only in a weakly stereoconvergent manner. However, changes in the amount of catalyst (up to 1 eq) affect either the regio‐ and stereoselectivity of the reaction, selectively leading to cis configured cyclopentenyl N9‐linked purine nucleosides, regardless the relative configuration (cis or trans) of the starting substrates. DFT studies clarified that this could be due to the low activation energy related to the crucial, Pd‐dependent π‐inversion step.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Stereoconvergent Synthesis of Cyclopentenyl Nucleosides by Palladium‐Assisted Allylic Reaction ; day:19 ; month:09 ; year:2022 ; extent:1
European journal of organic chemistry ; (19.09.2022) (gesamt 1)
- Urheber
-
Esposito, Anna
Talarico, Giovanni
De Fenza, Maria
D'Alonzo, Daniele
Guaragna, Annalisa
- DOI
-
10.1002/ejoc.202200708
- URN
-
urn:nbn:de:101:1-2022092015121898292815
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
- 15.08.2025, 07:26 MESZ
Datenpartner
Dieses Objekt wird bereitgestellt von:
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Esposito, Anna
- Talarico, Giovanni
- De Fenza, Maria
- D'Alonzo, Daniele
- Guaragna, Annalisa
Ähnliche Objekte (12)
Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction
Enantioselective Palladium-Catalyzed Allylic Dearomatization
Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Monosubstituted Indolin-3-ones
Mass spectrometric screening of chiral catalysts by monitoring the back reaction: Palladium-catalysed allylic substitution
Ortho-diphenylphosphanylbenzoyl-directed palladium catalyzed allylic substitution with soft nucleophiles
Palladium (0)-catalyzed amination of allylic natural terpenic functionalized olefins
Palladium-Catalyzed Asymmetric Synthesis of α,α-Disubstituted Allylic N-Arylamines
Allylsulfones through Palladium‐Catalyzed Allylic C−H Sulfonylation of Terminal Alkenes
Total Synthesis of (−)-Aspidospermidine via an Enantioselective Palladium-Catalysed Allylic Substitution Strategy
Palladium- and Iridium-Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles
Palladium‐ and Iridium‐Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles
Palladium-Catalyzed Reductive Heck Reaction
Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction
Enantioselective Palladium-Catalyzed Allylic Dearomatization
Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Monosubstituted Indolin-3-ones
Mass spectrometric screening of chiral catalysts by monitoring the back reaction: Palladium-catalysed allylic substitution
Ortho-diphenylphosphanylbenzoyl-directed palladium catalyzed allylic substitution with soft nucleophiles
Palladium (0)-catalyzed amination of allylic natural terpenic functionalized olefins
Palladium-Catalyzed Asymmetric Synthesis of α,α-Disubstituted Allylic N-Arylamines
Allylsulfones through Palladium‐Catalyzed Allylic C−H Sulfonylation of Terminal Alkenes
Total Synthesis of (−)-Aspidospermidine via an Enantioselective Palladium-Catalysed Allylic Substitution Strategy
Palladium- and Iridium-Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles
Palladium‐ and Iridium‐Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles
Palladium-Catalyzed Reductive Heck Reaction
Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction
Enantioselective Palladium-Catalyzed Allylic Dearomatization
Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Monosubstituted Indolin-3-ones
Mass spectrometric screening of chiral catalysts by monitoring the back reaction: Palladium-catalysed allylic substitution
Ortho-diphenylphosphanylbenzoyl-directed palladium catalyzed allylic substitution with soft nucleophiles
Palladium (0)-catalyzed amination of allylic natural terpenic functionalized olefins
Palladium-Catalyzed Asymmetric Synthesis of α,α-Disubstituted Allylic N-Arylamines
Allylsulfones through Palladium‐Catalyzed Allylic C−H Sulfonylation of Terminal Alkenes
Total Synthesis of (−)-Aspidospermidine via an Enantioselective Palladium-Catalysed Allylic Substitution Strategy
Palladium- and Iridium-Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles
Palladium‐ and Iridium‐Catalyzed Deracemization of Allylic Oxygen Compounds with Oxygen Nucleophiles