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Synthesis of prolinamide derivative as organocatalysts for asymmetric synthesis |
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| รหัสดีโอไอ | |
| Title | Synthesis of prolinamide derivative as organocatalysts for asymmetric synthesis |
| Creator | Sornpranart Sathapornvajana |
| Contributor | Tirayut Vilaivan |
| Publisher | Chulalongkorn University |
| Publication Year | 2549 |
| Keyword | Asymmetric synthesis, Proline -- Synthesis, Catalysts |
| Abstract | L-Prolinamide derivatives were synthesized from L-proline and 2-aminophenols with the objective to utilize additional H-bonding from the aminophenol in catalyzing asymmetric aldol reactions. Aldol reactions between various aromatic aldehydes and cyclohexanone in the presence of the best prolinamide derivatives afforded the aldol product with diastereoselectivity up to 95:5 (anti:syn) and enantioselectivity up to 95% (anti). Furthermore, the catalyst performance was evaluated in the direct aldol reaction in water. Reactions of aromatic aldehydes and cyclohexanone gave the aldol products with higher diasteroselectivity up to 94:6 (anti:syn) and enantioselectivity over 97% (anti) compared to reactions in organic solvents. A transition state model to explain the selectivity was also proposed. |
| URL Website | cuir.car.chula.ac.th |
