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Diastereomeric P*,N,S-tridentate diamidophosphites with a ferrocene moiety in asymmetric palladium catalysis
Journal of Organometallic Chemistry ( IF 2.1 ) Pub Date : 2020-02-27 , DOI: 10.1016/j.jorganchem.2020.121199
Konstantin N. Gavrilov , Ilya V. Chuchelkin , Vladislav S. Zimarev , Sergey V. Zheglov , Vladislav K. Gavrilov , Ilya D. Firsin , Alexander V. Maximychev , Alexander M. Perepukhov , Vladimir V. Chernyshev , Nataliya S. Goulioukina

Two novel diastereomeric P*,N,S-diamidophosphite ligands of the 1,3,2-diazaphospholidine series bearing a ferrocene moiety were synthesized in good yield. The use of these enantiopure ligands in the Pd-catalyzed allylic substitution of (E)-1,3-diphenylallyl acetate with CH2(CO2Me)2 and (CH2)4NH provided products with high enantiomeric excesses (up to 93% and 85% ee). Ee values up to 73% and 60% were obtained in the Pd-catalyzed allylic alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate or ethyl 2-acetamido-3-oxobutanoate, respectively. The efficiencies of the diastereomeric stereoselectors were compared.



中文翻译:

在不对称钯催化下具有二茂铁部分的非对映体P *,N,S-三齿二氨基亚磷酸酯

以高收率合成了具有二茂铁部分的1,3,2-二氮杂磷杂环戊烷系列的两个新的非对映体P *,N,S-二氨基亚磷酸酯配体。这些对映体纯配体在CH 2(CO 2 Me)2和(CH 24 NH的Pd催化的(E)-1,3-二苯基烯丙基乙酸酯的钯催化的烯丙基取代中的使用提供了高对映体过量的产物(最高93 %和85%ee)。e在肉桂酸与2-氧代环己烷-1-甲酸乙酯或2-乙酰氨基-3-氧代丁酸乙酯的乙酸催化的乙酸肉桂酯的烯丙基烷基化反应中,分别获得高达73%和60%的值。比较了非对映体立体选择器的效率。

更新日期:2020-02-27
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