Journal
JOURNAL OF CATALYSIS
Volume 282, Issue 1, Pages 112-119Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2011.06.004
Keywords
Chiral heterogeneous catalysts; Supported L-proline; Zirconium phosphates; Aldol addition; Aqueous medium
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Funding
- Ministero dell'Istruzione, dell'Universita e della Ricerca (MIUR)
- Firb-Futuro in Ricerca and the Universita degli Studi di Perugia
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Zirconium phosphates methyl and/or phenyl phosphonates-supported L-proline have been prepared as amorphous solids by precipitation of (4R)-4-(phosphonooxy)-L-proline, methyl and/or phenyl phosphonic acid with ZrOCl2. The supported L-proline catalysts were tested on the direct asymmetric aldol addition of cyclohexanone to p-nitrobenzaldehyde in DMF/H2O (9:1) and in sole water. The hydrophobic groups on solid surface favor reagents' diffusion toward proline chiral moiety increasing the catalytic activity of supported L-proline. High diastereoselectivity (anti/syn up to 94:6) and high enantiomeric excess up to 97% have been obtained. (C) 2011 Elsevier Inc. All rights reserved.
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