NOBIN-based chiral phosphite-type ligands and their application in asymmetric catalysis

被引：15

作者：

Gavrilov, Konstantin N. ^{[1
]}

Shiryaev, Alexei A. ^{[1
]}

Zheglov, Sergey V. ^{[1
]}

Bochelyuk, Marina S. ^{[1
]}

Chuchelkin, Ilya V. ^{[1
]}

Tafeenko, Viktor A. ^{[2
]}

Chernyshev, Vladimir V. ^{[2
,3
]}

Zamilatskov, Ilya A. ^{[3
]}

Mikhel, Igor S. ^{[3
]}

机构：

[1] Ryazan State Univ, Dept Chem, Ryazan 390000, Russia

[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[3] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Moscow 119071, Russia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 33期

基金：

俄罗斯科学基金会;

关键词：

Asymmetric allylic substitution; Palladium; Asymmetric conjugate addition; Copper; Phosphorus ligands; CONJUGATE ADDITION; ALLYLIC ALKYLATION; PHOSPHORAMIDITE LIGANDS; PHOSPHORUS LIGANDS; P; N LIGANDS; P-N; DIAMIDOPHOSPHITES; HYDROGENATION; COMPLEXES; SUBSTITUTION;

D O I：

10.1016/j.tetlet.2015.06.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

P*-Monodentate diamidophosphite and diastereomeric P,N-containing phosphite ligands have been synthesized from enantiomerically pure N-Bn-NOBIN and used as asymmetric inductors in Pd-catalyzed allylic substitution and Cu-catalyzed conjugate addition reactions. The best results (up to 93% ee) were obtained for the Pd-catalyzed allylic alkylation of (E)-1,3-diphenylallyl acetate with 1-cyclohexenylpyrrolidine. The reactions of P,N-containing ligands with Pd(COD)Cl-2 at molar ratios of L/M = 1 and 2 were studied using H-1, C-13, and P-31 NMR spectroscopy as well as HRESI mass spectrometry, showing the trans-PdCl2L2 complex was the only product. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4756 / 4761

页数：6

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