Chiral amido-oxazoline functionalized MCM-41: A sustainable heterogeneous catalyst for enantioselective Kharasch-Sosnovsky and Henry reactions.

Autor:	Tavakoli N; Department of Chemistry, Shahid Beheshti University, G.C., Tehran, 1983963113, Iran., Arvinnezhad H; Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, 66177-15175, Iran., Majidian S; Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, 66177-15175, Iran., Mahramasrar M; Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, 66177-15175, Iran., Jadidi K; Department of Chemistry, Shahid Beheshti University, G.C., Tehran, 1983963113, Iran., Samadi S; Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, 66177-15175, Iran.
Jazyk:	angličtina
Zdroj:	Heliyon [Heliyon] 2024 Oct 29; Vol. 10 (21), pp. e39911. Date of Electronic Publication: 2024 Oct 29 (Print Publication: 2024).
DOI:	10.1016/j.heliyon.2024.e39911
Abstrakt:	In this study, a series of chiral amido-oxazoline ligands was synthesized with a primary focus on immobilizing the most effective ligands on MCM-41 mesoporous material. Following several attempts, the para -nitro group of the chiral amido-oxazoline ligands was successfully reduced to amino group, enabling their immobilization on MCM-41. The resulting chiral heterogeneous amido-oxazoline ligands were characterized using various techniques, including FT-IR, XRD, TGA, SEM, TEM, EDX, and BET-BJH, confirming the successful immobilization of the amido-oxazoline ligands. A comparison of the efficiency of the homogeneous and heterogeneous amido-oxazoline-based ligands in the Kharasch-Sosnovsky and Henry reactions revealed better performance of the heterogeneous ligand. The immobilized amido-oxazoline-copper complexes exhibited remarkable catalytic activity, achieving excellent yields and enantioselectivities (up to 88 % ee ) in the Kharasch-Sosnovsky reaction, and delivering excellent yields with moderate enantioselectivities in the Henry reaction. Notably, the Henry reaction proceeded with moderate diastereoselectivity, favoring the syn diastereomer, under solvent-free conditions, highlighting the sustainability of the process. The heterogeneous nature of the catalysts facilitated effortless recovery and efficient reusability. Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Databáze:	MEDLINE
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