A recyclable organocatalyst for asymmetric Michael addition of acetone to nitroolefins |
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Authors: | Lu Aidang Liu Tao Wu Ronghua Wang Youming Wu Guiping Zhou Zhenghong Fang Jianxin Tang Chuchi |
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Affiliation: | State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China. |
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Abstract: | Based on different chiral diamine skeletons, a series of bifunctional primary amine-thiophosphoramides were synthesized and screened as the catalysts for the asymmetric Michael addition of acetone to both aromatic and aliphatic nitroolefins. Under the catalysis of a thiophosphoramide derived from 1,2-diphenylethane-1,2-diamine, the corresponding adducts were obtained in high yields (up to >99%) with excellent enantioselectivities (97-99% ee) under mild reaction conditions. Moreover, the catalyst could be recovered via simple phase separation and reused at least five times without any loss of both catalytic activity and stereocontrol. |
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