Shim Jae Ho, Lee Min Ji, Lee Min Ho, Kim Byeong-Seon, Ha Deok-Chan
Laboratory of Organic Synthesis, Department of Chemistry, Research Institute for Natural Sciences, Korea University Seoul 136-713 Korea
Department of Chemistry Education, Research Institute of Natural Science, Gyeongsang National University Jinju 52828 Korea
RSC Adv. 2020 Aug 27;10(53):31808-31814. doi: 10.1039/d0ra03550e. eCollection 2020 Aug 26.
Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (,)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, ()-Phenibut.
尽管迈克尔加成反应是一种非常著名且应用广泛的反应，但具有成本效益、无金属且易于制备的有机催化剂仍然很少见。一种手性、双功能、由（，）-1,2-二苯基乙二胺衍生的硫脲有机催化剂被开发出来，并应用于中性条件下硝基烯烃的不对称迈克尔加成反应。一般来说，氟取代硫脲催化剂在中性条件下表现出高化学产率和对映选择性。这些温和的反应对许多官能团具有耐受性，能提供良好到优异的产率，以及对迈克尔加成产物具有高非对映和对映选择性。通过生物活性化合物（）-苯丁胺的合成证明了该转化反应的实用性。
