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Issue 9, 2010
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Solvent-free direct enantioselective aldol reaction using polystyrene-supported N-sulfonyl-(Ra)-binam-D-prolinamide as a catalyst

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Abstract

The immobilization of N-sulfonyl-(Ra)-binam-D-prolinamide using polystyrene as a support allows the recovery of an efficient catalytic system for the enantioselective direct aldol reaction between different ketones and aldehydes under solvent-free or aqueous conditions. The polystyrene-supported N-sulfonyl-(Ra)-binam-D-prolinamide catalyst in combination with benzoic acid showed similar results to those obtained with unsupported N-tosyl-binam-derived prolinamide under similar reaction conditions. The aldol products were obtained at room temperature and using only 2 equivalents of the ketone with high yields, regio-, diastereo- and enantioselectivities. The aldol reaction between aldehydes can also be performed under these reaction conditions with moderate results. The recovered catalyst can be reused up to six times without having a detrimental effect on the achieved results.

Graphical abstract: Solvent-free direct enantioselective aldol reaction using polystyrene-supported N-sulfonyl-(Ra)-binam-d-prolinamide as a catalyst

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Publication details

The article was received on 12 Feb 2010, accepted on 01 Jul 2010 and first published on 04 Aug 2010


Article type: Paper
DOI: 10.1039/C002967J
Citation: Green Chem., 2010,12, 1599-1606
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    Solvent-free direct enantioselective aldol reaction using polystyrene-supported N-sulfonyl-(Ra)-binam-D-prolinamide as a catalyst

    A. Bañón-Caballero, G. Guillena and C. Nájera, Green Chem., 2010, 12, 1599
    DOI: 10.1039/C002967J

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