Novel Prolinamide-Supported Polystyrene as Highly Stereoselective and Recyclable Organocatalyst for the Aldol Reaction

A new prolinamide derivative anchored to a polystyrene support has been straightforwardly prepared and employed as heterogeneous catalyst in the direct asymmetric aldol reaction with good results in terms of yield and stereoselectivity. The optimal reaction conditions were found when a 1:2 (v/v) wat...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2008-06, Vol.350 (9), p.1397-1405
Main Authors: Gruttadauria, Michelangelo, Giacalone, Francesco, Marculescu, Adriana Mossuto, Noto, Renato
Format: Article
Language:English
Subjects:
aldol reactions
immoblization
organic catalysis
polymers
proline
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Summary:A new prolinamide derivative anchored to a polystyrene support has been straightforwardly prepared and employed as heterogeneous catalyst in the direct asymmetric aldol reaction with good results in terms of yield and stereoselectivity. The optimal reaction conditions were found when a 1:2 (v/v) water/chloroform mixture was used. This mixture was the best compromise between the good swelling properties of chloroform and the formation of a concentrated organic phase due to the presence of water. Noticeably, the enantioselectivities obtained employing acetone as ketone were, to the best of our knowledge, the highest achieved with a supported proline derivative. This catalyst can be easily recovered, regenerated and recycled, without loss of activity, at least for twelve cycles.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800090