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
相关论文
共 50 条
  • [21] Pd-Catalyzed Asymmetric Hydrogenolysis Rearrangement of Allylic Esters to Access Axially Chiral Olefins
    Shao, Bing-Ru
    Jiang, Wen-Feng
    Wang, Chen
    Shi, Lei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (07)
  • [22] Phosphorylated (S)-tert-leucinol isophthalic diamide as a ligand for Pd-catalyzed asymmetric allylic substitution
    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
  • [23] Pd-catalyzed asymmetric α-allylic alkylation of thioamides
    Rong, Bin
    Yang, Qin
    Liu, Yong
    Xu, Hong
    Hu, Yifan
    Cheng, Xuejing
    Zhao, Baoguo
    TETRAHEDRON LETTERS, 2015, 56 (04) : 595 - 598
  • [24] A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters
    Albat, Dominik
    Neudoerfl, Joerg-Martin
    Schmalz, Hans-Guenther
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (14) : 2099 - 2102
  • [25] Diastereomeric P,N-bidentate amidophosphites based on (S,S)- and (R,R)-hydrobenzoin as ligands in the Pd-catalyzed asymmetric allylation
    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
  • [26] Pd-Catalyzed Asymmetric Larock Indole Synthesis to Access Axially Chiral N-Arylindoles
    Zhang, Genwei
    Yang, Bin
    Yang, Junfeng
    Zhang, Junliang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (08) : 5493 - 5501
  • [27] Construction of tertiary chiral centers by Pd-catalyzed asymmetric allylic alkylation of prochiral enolate equivalents
    Kita, Yusuke
    Numajiri, Yoshitaka
    Okamoto, Noriko
    Stoltz, Brian M.
    TETRAHEDRON, 2015, 71 (37) : 6349 - 6353
  • [28] Enantioconvergent synthesis of axially chiral amides enabled by Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation
    Su, Lei
    Gao, Shen
    Liu, Jiawang
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [29] 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
    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
  • [30] Chiral thioimidazoline ligands for palladium-catalyzed asymmetric allylation
    Morimoto, T
    Tachibana, K
    Achiwa, K
    SYNLETT, 1997, (07) : 783 - &
12345