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Novel Prolinamide‐Supported Polystyrene as Highly Stereoselective and Recyclable Organocatalyst for the Aldol Reaction
Author(s) -
Gruttadauria Michelangelo,
Giacalone Francesco,
Marculescu Adriana Mossuto,
Noto Renato
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800090
Subject(s) - chemistry , aldol reaction , acetone , polystyrene , chloroform , stereoselectivity , catalysis , ketone , yield (engineering) , derivative (finance) , organocatalysis , organic chemistry , enantioselective synthesis , polymer chemistry , polymer , materials science , economics , financial economics , metallurgy
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.