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

页码：2278 / 2285

页数：8

共 50 条

[21] Pd-Catalyzed Enantioselective C-H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines [J].

Chu, Ling ;

Wang, Xiao-Chen ;

Moore, Curtis E. ;

Rheingold, Arnold L. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) :16344-16347

[22] Pd-Catalyzed Asymmetric Hydrogenolysis Rearrangement of Allylic Esters to Access Axially Chiral Olefins [J].

Shao, Bing-Ru ;

Jiang, Wen-Feng ;

Wang, Chen ;

Shi, Lei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (07)

[23] Phosphorylated (S)-tert-leucinol isophthalic diamide as a ligand for Pd-catalyzed asymmetric allylic substitution [J].

Gavrilov, K. N. ;

Zheglov, S. V. ;

Groshkin, N. N. ;

Gavrilov, V. K. ;

Maksimova, M. G. ;

Volov, A. N. ;

Zamilatskov, I. A. .

RUSSIAN CHEMICAL BULLETIN, 2014, 63 (12) :2635-2640

[24] Pd-catalyzed asymmetric α-allylic alkylation of thioamides [J].

Rong, Bin ;

Yang, Qin ;

Liu, Yong ;

Xu, Hong ;

Hu, Yifan ;

Cheng, Xuejing ;

Zhao, Baoguo .

TETRAHEDRON LETTERS, 2015, 56 (04) :595-598

[25] A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters [J].

Albat, Dominik ;

Neudoerfl, Joerg-Martin ;

Schmalz, Hans-Guenther .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (14) :2099-2102

[26] Diastereomeric P,N-bidentate amidophosphites based on (S,S)- and (R,R)-hydrobenzoin as ligands in the Pd-catalyzed asymmetric allylation [J].

K. N. Gavrilov ;

I. V. Chuchelkin ;

S. V. Zheglov ;

N. N. Groshkin ;

I. M. Novikov ;

E. A. Rastorguev ;

V. A. Davankov .

Russian Chemical Bulletin, 2011, 60 :2063-2067

[27] Pd-Catalyzed Asymmetric Larock Indole Synthesis to Access Axially Chiral N-Arylindoles [J].

Zhang, Genwei ;

Yang, Bin ;

Yang, Junfeng ;

Zhang, Junliang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (08) :5493-5501

[28] Construction of tertiary chiral centers by Pd-catalyzed asymmetric allylic alkylation of prochiral enolate equivalents [J].

Kita, Yusuke ;

Numajiri, Yoshitaka ;

Okamoto, Noriko ;

Stoltz, Brian M. .

TETRAHEDRON, 2015, 71 (37) :6349-6353

[29] Enantioconvergent synthesis of axially chiral amides enabled by Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation [J].

Su, Lei ;

Gao, Shen ;

Liu, Jiawang .

NATURE COMMUNICATIONS, 2024, 15 (01)

[30] Development of P*-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations [J].

Gavrilov, Konstantin N. ;

Shiryaev, Alexei A. ;

Zheglov, Sergey V. ;

Potapova, Oksana V. ;

Chuchelkin, Ilya V. ;

Novikov, Ivan M. ;

Rastorguev, Eugenie A. ;

Davankov, Vadim A. .

TETRAHEDRON-ASYMMETRY, 2013, 24 (07) :409-417

← 1 2 3 4 5 →