Organocatalytic Michael addition of aldehydes to trisubstituted nitroolefins |
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Authors: | Leilei Wang Xiaojing Zhang Dawei Ma |
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Institution: | 1. Shenyang Pharmaceutical University, 103 Wenhua Lu, Shenyang 110016, China;2. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China |
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Abstract: | The combination of O-TMS protected diphenyl-prolinol and benzoic acid was found to be effective to catalyze the Michael addition of aldehydes to 3-substituted 3-nitroacrylates. The reaction provided syn,anti-Michael adducts with good diastereoselectivity and excellent enantioselectivity. Some β-aryl and α-methyl substituted nitroolefins also worked under these conditions, although prolonging reaction time was required. These adducts could be used for assembling 2,3,4-trisubstituted pyrrolidines through simple hydrogenation. |
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