RT Journal Article
T1 Theoretical exploration of a diene-transmissive hetero-Diels–Alder strategy to synthesize boron-functionalized octahydroquinolines
A1 Rafik, Amine
A1 Jaddi, Abdeljabbar
A1 Abbiche, Khalid
A1 Salah, Mohammed
A1 Carvajal Zaera, Miguel
A1 Marakchi, Khadija
AB A diene-transmissive hetero-Diels–Alder strategy, grounded in previous experimental works and employing boronated dienophiles, is proposed for the synthesis of boron-bearing octahydroquinolines. To assess its feasibility, three representative reactions were investigated, and their thermodynamics were evaluated in toluene and acetonitrile at various temperatures using the ωB97X-D level of theory. The peri-, regio-, stereo-, and π-facial selectivities were predicted. The reaction mechanisms were elucidated through exploration of the reaction pathways and topological studies using the Electron Localization Function and Independent Gradient Model. The predictions are consistent with available experimental work and show that the reactions are feasible with low to moderate polarity. The results also demonstrate that the selectivity of the reactions can in some cases be tuned by judicious choice of reaction conditions to deliver specific products with high selectivity.
PB Royal Society of Chemistry
SN 1477-0520
SN 1477-0539 (identificadores)
YR 2026
FD 2026
LK https://hdl.handle.net/10272/28020
UL https://hdl.handle.net/10272/28020
LA eng
NO Rafik, A., Jaddi, A., Abbiche, K., Salah, M., Carvajal, M., & Marakchi, K. (2026). Theoretical exploration of a diene-transmissive hetero-Diels–Alder strategy to synthesize boron-functionalized octahydroquinolines. Organic & Biomolecular Chemistry, 24(2), 369–384. https://doi.org/10.1039/d5ob01638j
NO This work has received funding from the European Union’s Horizon 2020 research and innovation program under Marie Sklodowska-Curie grant agreement no. 872081, and grant PID2022-136228NB-C21 funded by MICIU/AEI/10.13039/ 501100011033 and, as appropriate, by ERDF A way of making Europe, by ERDF/EU, by the European Union or by the European Union NextGenerationEU/PRTR. This work is also supported by the Consejería de Transformación Económica, Industria, Conocimiento y Universidades, Junta de Andalucía and European Regional Development Fund (ERDF 2021–2027) under the project EPIT1462023. The authors acknowledge the Moroccan Association of Theoretical Chemists for providing the computational programs.
DS Repositorio Institucional de la Universidad de Huelva
RD 31 may 2026