Prolinamides derived from aminophenols as organocatalysts for asymmetric direct aldol reactions |
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| Authors: | Sornpranart Sathapornvajana |
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| Institution: | Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand |
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| Abstract: | N-(2-Hydroxyphenyl)-prolinamides were synthesized with the aim to introduce an additional hydrogen bonding site to the prolinamide structure. These compounds were evaluated as organocatalysts for asymmetric aldol reactions between aromatic aldehydes and cyclohexanone. Very good yields, diastereoselectivities, and enantioselectivities were achieved in both organic solvents and water. The importance of the additional hydrogen bonding site was confirmed by comparative experiments with prolinamide derivatives without the hydroxyl group. |
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| Keywords: | Aldol reaction Asymmetric catalysis Proline Organocatalysts Hydrogen bonding |
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