Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes |
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| Institution: | 1. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, PR China;2. Department of Pathology, King Medical Diagnostics Center, Guangzhou 510330, PR China;1. Center for Air Resources Engineering and Science, Clarkson University, Potsdam, NY 13699, USA;2. Department of Chemical and Biomolecular Engineering, Clarkson University, Potsdam, NY 13699, USA |
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| Abstract: | Two chiral aromatic l-prolinamides were synthesized in high overall yield (95%) from N-Boc-l-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). |
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