手性 Cp-铱(III)催化剂与手性羧酸在亚磷酸酯的对映选择性 C-H 酰胺化反应中的协同作用。
Cooperative Effects between Chiral Cp -Iridium(III) Catalysts and Chiral Carboxylic Acids in Enantioselective C-H Amidations of Phosphine Oxides.
机构信息
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-1015, Lausanne, Switzerland.
Current address: Syngenta Crop Protection AG, Schaffhauserstr., CH-4332, Stein, Switzerland.
出版信息
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15088-15092. doi: 10.1002/anie.201708440. Epub 2017 Oct 6.
An enantioselective C-H amidation of phosphine oxides by using an iridium(III) catalyst bearing an atropchiral cyclopentadienyl (Cp ) ligand is reported. A very strong cooperative effect between the chiral Cp ligand and a phthaloyl tert-leucine enabled the transformation. Matched-mismatched cases of the different acid enantiomers are shown. The amidated P-chiral arylphosphine oxides are formed in yields of up to 95 % and with excellent enantioselectivities of up to 99:1 er. Enantiospecific reduction provides access to valuable P-chiral phosphorus(III) compounds.
本文报道了一种手性铱(III)催化剂催化的磷氧化物的对映选择性 C-H 酰胺化反应，该催化剂带有一个轴手性环戊二烯基（Cp）配体。手性 Cp 配体和邻苯二甲酰基叔亮氨酸之间存在很强的协同效应，使得该转化得以实现。对不同酸对映异构体的匹配-不匹配情况进行了研究。所形成的磷手性芳基磷氧化物的产率高达 95%，对映选择性高达 99:1 er。对映选择性还原可获得有价值的磷手性磷(III)化合物。
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