A highly regio- and stereoselective route to d- and l-cyclohexenyl nucleosides has been devised, using the Tsuji–Trost reaction as the key step. Contrarily to the widely accepted mechanism (involving a net retention of configuration), the reaction proceeded in a highly stereoconvergent manner, providing cis nucleosides regardless of the relative configuration of the starting materials. DFT calculations confirmed the experimental data while suggesting the origin of the stereochemical reaction outcome.
A Stereoconvergent Tsuji–Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides / Esposito, Anna; di Giovanni, C.; De Fenza, M.; Talarico, G.; Chino, M.; Palumbo, G.; Guaragna, A.; D'Alonzo, D.. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 26:12(2020), pp. 2597-2601. [10.1002/chem.201905367]
A Stereoconvergent Tsuji–Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides
Esposito AnnaPrimo
;De Fenza M.;Talarico G.;Chino M.;Palumbo G.;Guaragna A.
;D'Alonzo D.
2020
Abstract
A highly regio- and stereoselective route to d- and l-cyclohexenyl nucleosides has been devised, using the Tsuji–Trost reaction as the key step. Contrarily to the widely accepted mechanism (involving a net retention of configuration), the reaction proceeded in a highly stereoconvergent manner, providing cis nucleosides regardless of the relative configuration of the starting materials. DFT calculations confirmed the experimental data while suggesting the origin of the stereochemical reaction outcome.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
