Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 347, Issue 15, Pages 1948-1952Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505247
Keywords
asymmetric aldol reaction; C-C bond formation; organic catalysis; proline; thioamides
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A series of novel L-proline derived thioamides has been synthesised. They have been evaluated as organocatalysts in the direct asymmetric aldol reaction for the first time. Thioamides exhibit catalytic ability higher than proline itself and the model aldol reaction of 4-cyanobenzaldehyde with acetone proceeds well in the presence of 5 mol % of catalyst (ee up to 100%). Other aromatic aldehydes gave aldol products with high ees and moderate yields. Small changes in the catalyst's structure [e.g., N-Bn versus N-CH(CH3)Ph] as well as the addition of an acid have a profound effect on their activity. The unexpected formation of the catalyst-derived cyclic adducts was observed and their reactivity was established giving valuable insight into the course of the reaction.
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