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A Stereoconvergent Tsuji–Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides
Author(s) -
Esposito Anna,
Giovanni Concetta,
De Fenza Maria,
Talarico Giovanni,
Chino Marco,
Palumbo Giovanni,
Guaragna Annalisa,
D'Alonzo Daniele
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905367
Subject(s) - stereoselectivity , chemistry , stereochemistry , combinatorial chemistry , reaction mechanism , organic chemistry , catalysis
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.