Direct asymmetric aldol reaction co-catalyzed by l-proline and group 12 elements Lewis acids in the presence of water |
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| Authors: | Maë l Penhoat,Didier BarbryChristian Rolando |
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| Affiliation: | Miniaturization for Synthesis, Analysis and Proteomics, USR CNRS 3290 and Institut Eugène-Michel Chevreul, FR CNRS 2638, Université de Lille 1, Sciences et Technologies, 59655 Villeneuve d’Ascq, France |
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| Abstract: | An approach based on combinations of various water compatible Lewis acids and l-proline co-catalysts has been evaluated for the direct asymmetric aldol reaction. From this broad screening, chloride salts from group 12 elements (ZnCl2, CdCl2, HgCl2) lead to the highest stereoselectivities. Optimized catalytic conditions (catalytic system: l-proline: 20%/ZnCl2: 10%; solvent mixture: DMSO/H2O, 8:2) gave anti aldol products with improved enantioselectivity (>99% ee) compared to a moderately stereoselective procedure based on proline activation only. |
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| Keywords: | Aldol reaction Dual activation Lewis acids Proline |
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