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Chiral Hybrid Inorganic–Organic Materials: Synthesis, Characterization, and Application in Stereoselective Organocatalytic Cycloadditions

Author:
Puglisi, Alessandra, Benaglia, Maurizio, Annunziata, Rita, Chiroli, Valerio, Porta, Riccardo, Gervasini, Antonella
Source:
Journal of organic chemistry 2013 v.78 no.22 pp. 11326-11334
ISSN:
1520-6904
Subject:
aldehydes, catalysts, catalytic activity, centrifugation, copper, esters, filtration, nanoparticles, nitrogen, nuclear magnetic resonance spectroscopy, organic chemistry, phenylalanine, porous media, scanning electron microscopy, silica, stereoselectivity, tyrosine
Abstract:
The synthesis of chiral imidazolidinones on mesoporous silica nanoparticles, exploiting two different anchoring sites and two different linkers, is reported. Catalysts 1–4 were prepared starting from l-phenylalanine or l-tyrosine methyl esters and supporting the imidazolidinone onto silica by grafting protocols or azide–alkyne copper(I)-catalyzed cycloaddition. The four catalysts were fully characterized by solid-state NMR, N₂ physisorption, SEM, and TGA in order to provide structural assessments, including an evaluation of surface areas, pore dimensions, and catalyst loading. They were used in organocatalyzed Diels–Alder cycloadditions between cyclopentadiene and different aldehydes, affording results comparable to those obtained with the nonsupported catalyst (up to 91% yield and 92% ee in the model reaction between cyclopentadiene and cinnamic aldehyde). The catalysts were recovered from the reaction mixture by simple filtration or centrifugation. The most active catalyst was recycled two times with some loss of catalytic efficiency and a small erosion of ee.
Agid:
5500705