Silica nanoparticles of different morphological properties were functionalized with enantiomerically pure imidazolidinones, through different immobilization techniques; stainless-steel columns were then loaded with silica bearing chiral organocatalysts to realize chiral “homemade” reactors. The influence of the material properties and immobilization procedures on the chemical and stereochemical activities of the chiral HPLC columns was studied by performing organocatalyzed Diels[BOND]Alder reactions between cyclopentadiene and α,β-unsaturated aldehydes under continuous-flow conditions. In some cases, excellent enantioselectivities were obtained, thus showing that a catalytic reactor may work efficiently to continuously produce enantiomerically enriched cycloadducts for more than 200 h. Regeneration of the organocatalytic column was also partially accomplished, although associated with a slightly lower enantioselectivity, thus prolonging the “life” of the reactor to more than 300 h.

Stereoselective Diels-Alder reactions promoted under continuous-flow conditions by silica-supported chiral organocatalysts / R. Porta, M. Benaglia, V. Chiroli, F. Coccia, A. Puglisi. - In: ISRAEL JOURNAL OF CHEMISTRY. - ISSN 0021-2148. - 54:4(2014), pp. 381-394. [10.1002/ijch.201300106]

Stereoselective Diels-Alder reactions promoted under continuous-flow conditions by silica-supported chiral organocatalysts

R. Porta
Primo
;
M. Benaglia
;
V. Chiroli;F. Coccia
Penultimo
;
A. Puglisi
Ultimo
2014

Abstract

Silica nanoparticles of different morphological properties were functionalized with enantiomerically pure imidazolidinones, through different immobilization techniques; stainless-steel columns were then loaded with silica bearing chiral organocatalysts to realize chiral “homemade” reactors. The influence of the material properties and immobilization procedures on the chemical and stereochemical activities of the chiral HPLC columns was studied by performing organocatalyzed Diels[BOND]Alder reactions between cyclopentadiene and α,β-unsaturated aldehydes under continuous-flow conditions. In some cases, excellent enantioselectivities were obtained, thus showing that a catalytic reactor may work efficiently to continuously produce enantiomerically enriched cycloadducts for more than 200 h. Regeneration of the organocatalytic column was also partially accomplished, although associated with a slightly lower enantioselectivity, thus prolonging the “life” of the reactor to more than 300 h.
Chirality; Cycloaddition; Flow chemistry; Organocatalysis; Supported catalysts
Settore CHIM/06 - Chimica Organica
   Multifucntional hybrid materials as novel chiral recyclable catalysts for one-pot, multistep synthesis of structurally complex molecules
   FONDAZIONE CARIPLO
   2011-0293

   Materiali ibridi multifunzionali per lo sviluppo di processi catalitici sostenibili
   MINISTERO DELL'ISTRUZIONE E DEL MERITO
   RBFR10BF5V_003
2014
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/235286
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