Asymmetric aza-Michael reactions catalyzed by cinchona alkaloids |
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Authors: | Perdicchia Dario Jørgensen Karl Anker |
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Affiliation: | Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark. |
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Abstract: | The organocatalysed asymmetric aza-Michael addition of hydrazones to cyclic enones has been achieved in good yield and stereoselection using cheap and commercially available cinchona alkaloids as catalysts. A systematic study of the influence of the structure of the enone on the stereoselectivity was carried out, leading to optically active products with up to 77% ee. The products can be recrystallized to give nearly enantiopure products, and furthermore it was shown that the products could be reduced to the corresponding 1,3-benzylidenehydrazino alcohol derivatives with high diastereoselectivity. |
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