Institut de Chimie Moléculaire et des Matériaux d'Orsay

Chimie Peptidomimétique Photochimie, Procédés Alternatifs - CP3A

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Procédés alternatifs et chimie verte

Heterogeneous asymmetric organocatalysis

We have developed a novel heterogeneous chiral catalyst by grafting cupreine onto amorphous silica. Cupreine (CPN) was readily prepared in one step from commercially available quinine then grafted to the silica support through a thioether bond involving the 3-mercaptopropyl triethoxysilane (MPTES) as a linker between the catalyst and silica.

Our results attested for the first time that silica is a suitable support to immobilise CPN while retaining the asymmetric catalytic performance of this bifuctional catalyst almost unchanged for the asymmetric Michael addition of malonate to trans-beta-nitrostyrene in some biomass-derived solvents. We are now investigating the use of Si-CPN for various applications under continuous flow conditions.

reference: Cupreine grafted onto silica as an enantioselective and recyclable catalyst for the 1,4-addition of malonate to trans-beta-nitrostyrene, I. Billault, R. Launez and M.-C. Scherrmann, RSC Adv., 2015, 5, 29386–29390. DOI: 10.1039/c5ra02292d