Recyclable silica-supported prolinamide organocatalysts for direct asymmetric Aldol reaction in waterElectronic supplementary information (ESI) available: Characterization of supported organocatalysts M2-M5; preparation of non-silylated organocatalysts analogues; catalytic tests with homogeneous organocatalysts 6 and 7; spectroscopic data of compounds 4 and 9; NMR and IR spectra of compounds. See DOI: 10.1039/c2gc35227cThis article is dedicated to Prof. Miguel A. Miranda on the occasion of his 6

• Main Authors: Monge-Marcet, Amàlia, Cattoën, Xavier, Alonso, Diego A, Nájera, Carmen, Man, Michel Wong Chi, Pleixats, Roser
• Format: Article
• Language: English
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c2gc35227c

Asymmetric organocatalytic materials based on a prolinamide scaffold have been synthesized according to different synthetic routes from a monosilylated precursor: simple or surfactant-assisted co-condensation and grafting on preformed mesostructured silica. The catalytic properties of these materials have been compared for direct asymmetric aldol reactions. The best catalytic material results from a simple co-condensation without structure-directing agent. Simple and green conditions are used for the aldol reaction, the process being performed in water at room temperature, with relatively low amounts of supported organocatalysts and in the absence of an acid co-catalyst. Good recyclabilities are observed without the need for catalyst regeneration, with enantioselectivities (ee up to 92%) higher than that of the parent homogeneous catalysts. Catalytic organosilicas based on a prolinamide scaffold exhibit high asymmetric inductions and good recyclabilities for direct aldol reactions in water.