160583-98-2Relevant academic research and scientific papers
Regio- And Stereoselective Hydroiodination of Internal Alkynes with Ex Situ-Generated HI
Nozawa-Kumada, Kanako,Noguchi, Koto,Akada, Tomoya,Shigeno, Masanori,Kondo, Yoshinori
supporting information, p. 6659 - 6663 (2021/09/08)
Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.
A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes
Bartoli, Giuseppe,Cipolletti, Roberto,Di Antonio, Giustino,Giovannini, Riccardo,Lanari, Silvia,Marcolini, Mauro,Marcantoni, Enrico
experimental part, p. 3509 - 3517 (2010/08/21)
The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl3 promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl3·7H2O-NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon-carbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid 1, named (R)-Tiagabine, which is a potent and selective γ-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans. The Royal Society of Chemistry 2010.
