Chiral amido- and diamidophosphites with a peripheral pyridine ring in Pd-catalyzed asymmetric allylation

被引：6
|
作者：
Gavrilov, K. N. [1 ]
Zheglov, S. V. [1 ]
Novikov, I. M. [1 ]
Gavrilov, V. K. [1 ]
Zamilatskov, I. A. [2 ]
Mikhel, I. S. [2 ]
机构：
[1] SA Esenin Ryazan State Univ, 46 Ul Svobody, Ryazan 390000, Russia
[2] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Bldg 4,31 Leninsky Prosp, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2016年 / 65卷 / 09期
基金：
俄罗斯科学基金会;
关键词：
chiral amidophosphites; chiral diamidophosphites; asymmetric allylation; palladium catalysts; zinc(II) 5,10,15,20-tetraphenylporphyrinate; ALLYLIC SUBSTITUTION; ENANTIOSELECTIVE ALLYLATION; PHOSPHORAMIDITE LIGANDS; MONODENTATE PHOSPHITE; PHOSPHORUS LIGANDS; COMPLEXES; HYDROGENATION; EFFICIENT; HYDROFORMYLATION; HYDROBORATION;
D O I：
10.1007/s11172-016-1578-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
New chiral amidophosphite and diamidophosphite ligands with exocyclic pyridyl-containing substituents were obtained. Their efficiency in the Pd-catalyzed enantioselective allylic substitution was compared: in the sulfonylation of (E)-1,3-diphenylallyl acetate with sodium p-toluenesulfinate, the ee can reach 77%; its alkylation with dimethyl malonate and amination with pyrrolidine gave up to 80% and 74% ee, respectively. The asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexanecarboxylate can provide to 68% ee. The complexation of zinc(ii) 5,10,15,20-tetraphenylporphyrinate with diamidophosphite ligand and its influence on conversion and enantioselectivity of the process were studied.
引用
收藏
页码：2278 / 2285
页数：8
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