175398-36-4Relevant academic research and scientific papers
A Stereoconvergent Tsuji–Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides
Chino, Marco,D'Alonzo, Daniele,De Fenza, Maria,Esposito, Anna,Guaragna, Annalisa,Palumbo, Giovanni,Talarico, Giovanni,di Giovanni, Concetta
, (2019)
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 chemoenzymatic preparation of both enantiomers of ω-hydroxymethyl-substituted lactones
Buisson, Didier,Azerad, Robert
, p. 9 - 12 (2007/10/03)
(R)- and (S)-δ-hydroxymethyl valerolactone and ε-hydroxymethyl caprolactone were prepared as tert-butyldiphenylsilyl derivatives, in good yield and high enantiomeric purities, in a 5 step sequence, starting from the microbial stereospecific reduction of ethyl 2-oxocyclopentane or 2-oxocyclohexane carboxylates respectively.
