Advances towards highly active and stereoselective simple and cheap proline-based organocatalysts

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Ten 4-acyloxy-L-prolines were screened as catalysts at loadings of 2–0.1 mol-% for the direct asymmetric aldol reaction in water by using variable amounts of water. Among them, a new catalyst, the L-proline carrying a trans-4-(2,2-diphenylacetoxy)group, and a catalyst previously synthesized by us, the L-proline carrying a trans-(4-phenylbutanoyloxy)group, were found to be excellent catalysts for the aldol reactionbetween cyclohexanone or cyclopentanone and substituted benzaldehydes when employed in only 1 and 0.5 mol-%,respectively, at room temperature without additives. For such catalysts, high turnover numbers were obtained, which are among the highest values obtained for enamine organocatalysis.Finally, these catalysts can be synthesized by direct O-acylation from inexpensive molecules and successfully used in scaled-up reactions.
Lingua originaleEnglish
pagine (da-a)5696-5704
Numero di pagine9
RivistaEuropean Journal of Organic Chemistry
Stato di pubblicazionePublished - 2010

All Science Journal Classification (ASJC) codes

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