A Recyclable Organocatalyst for Asymmetric Michael Addition of Acetone to Nitroolefins

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• 作者：Aidang Lu ; Tao Liu ; Ronghua Wu ; Youming Wang ; Guiping Wu ; Zhenghong Zhou ; Jianxin Fang ; Chuchi Tang
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：May 20, 2011
• 年：2011
• 卷：76
• 期：10
• 页码：3872-3879
• 全文大小：869K
• 年卷期：v.76,no.10(May 20, 2011)
• ISSN：1520-6904

文摘

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鈭?9% 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.