Polystyrene-supported proline and prolinamide. Versatile heterogeneous organocatalysts both for asymmetric aldol reaction in water and α-selenenylation of aldehydes

A simple and efficient synthesis of polystyrene-supported proline and prolinamide has been carried out. Polystyrene-supported proline has been used as organocatalyst in the asymmetric aldol reaction between cyclohexanone and substituted benzaldehydes in water without any additive. High yields, diast...

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Bibliographic Details
Published in:Tetrahedron letters 2007, Vol.48 (2), p.255-259
Main Authors: Giacalone, Francesco, Gruttadauria, Michelangelo, Marculescu, Adriana Mossuto, Noto, Renato
Format: Article
Language:English
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Summary:A simple and efficient synthesis of polystyrene-supported proline and prolinamide has been carried out. Polystyrene-supported proline has been used as organocatalyst in the asymmetric aldol reaction between cyclohexanone and substituted benzaldehydes in water without any additive. High yields, diastereoselectivities and ee values have been observed. The versatility of this resin was demonstrated in the α-selenenylation of aldehydes. Both proline and prolinamide resins gave high yields. Recycling studies showed that the proline resin gave better results than prolinamide resin.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.11.040