Stoichiometric Tsuji-Trost reaction of cyclopentenyl carbonates proceeds in stereoconvergent manner, selectively leading to cis configured nucleosides, regardless the relative configuration (cis or trans) of the starting substrates. As indicated by DFT calculations, the reaction outcome relies on the low activation energy related to the crucial, Pd-dependent π-inversion step. This approach may represent a useful strategy for the synthesis of bioactive carbocyclic nucleosides.
Stereoconvergent Synthesis of Cyclopentenyl Nucleosides by Palladium‐Assisted Allylic Reaction / Esposito, Anna; Talarico, Giovanni; DE FENZA, Maria; D'Alonzo, Daniele; Guaragna, Annalisa. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2022:48(2022), p. e202200708. [10.1002/ejoc.202200708]
Stereoconvergent Synthesis of Cyclopentenyl Nucleosides by Palladium‐Assisted Allylic Reaction
Anna Esposito
;Giovanni Talarico;Maria De Fenza;Daniele D'Alonzo
;Annalisa Guaragna
2022
Abstract
Stoichiometric Tsuji-Trost reaction of cyclopentenyl carbonates proceeds in stereoconvergent manner, selectively leading to cis configured nucleosides, regardless the relative configuration (cis or trans) of the starting substrates. As indicated by DFT calculations, the reaction outcome relies on the low activation energy related to the crucial, Pd-dependent π-inversion step. This approach may represent a useful strategy for the synthesis of bioactive carbocyclic nucleosides.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
