Theoretical Exploration of the Diene-Transmissive Hetero-Diels-Alder Strategy Toward Boron-Functionalized Octahydroquinolines
Amine Rafik, Abdeljabbar Jaddi, Khalid Abbiche, Mohammed Salah, Miguel Carvajal, Khadija Marakchi
Published: 2025/10/2
Abstract
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 WB97X-D level of theory. The peri-, regio-, stereo-, and $\pi$-facial selectivities were predicted. The reactions mechanisms were elucidated through exploration of the reaction pathways. The predictions are consistent with available experimental work, and show the reactions are feasible with low to moderate polarity. The results also demonstrate that the reactions selectivity can in some cases be tuned by judicious choice of reaction conditions to deliver specific products with high selectivity.