Diamidophosphite based on (1R,2R)-1,2-bis(3-hydroxybenzamido)cyclohexane in Pd-catalyzed enantioselective allylation

被引：4
|
作者：
Gavrilov, K. N. [1 ]
Zheglov, S. V. [1 ]
Gavrilov, V. K. [1 ]
Zamilatskov, I. A. [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, 31 Leninsky Prosp, Moscow 119071, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2016年 / 65卷 / 03期
基金：
俄罗斯基础研究基金会;
关键词：
diamines; diamides; diamidophosphites; palladium catalysts; asymmetric allylation; ASYMMETRIC ALLYLIC ALKYLATION; 3+2 CYCLOADDITION; MONODENTATE PHOSPHITE; CONTAINING LIGANDS; COMPLEXES; HYDROGENATION; EFFICIENT; SUBSTITUTION;
D O I：
10.1007/s11172-016-1355-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Diamidophosphite ligand bearing (1R,2R)-1,2-bis(3-hydroxybenzamido)cyclohexane fragment and stereogenic phosphorus atoms in the 1,3,2-diazaphopholidine cycles was synthesized. Catalytic performance of this ligand was evaluated in asymmetric allylic substitution. In the reactions involving (E)-1,3-diphenyl allyl acetate as a substrate, up to 94% ee in alkylation with dimethyl malonate and up to 68% ee in amination with pyrrolidine was achieved in the presence of this ligand.
引用
收藏
页码：680 / 684
页数：5
相关论文
共 50 条
  • [1] Diamidophosphite based on (1R,2R)-1,2-bis(3-hydroxybenzamido)cyclohexane in Pd-catalyzed enantioselective allylation
    K. N. Gavrilov
    S. V. Zheglov
    V. K. Gavrilov
    I. A. Zamilatskov
    Russian Chemical Bulletin, 2016, 65 : 680 - 684
  • [2] Bis[(1R,2R)-(-)-1,2-bis(trimethylsilylamino)-cyclohexane(2-)-κ2N,N′]zirconium(IV)
    Li, JF
    Weng, LH
    Huang, SP
    Tong, HB
    Liu, DS
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2002, 58 : M510 - M512
  • [3] (1R,2R)-(-)-1,2-Dibenzamidino-cyclohexane
    Li, JF
    Weng, LH
    Huang, SP
    Tong, HB
    Liu, DS
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 : O1078 - O1080
  • [4] (1R,2R)-bis(4-pyridylmethyleneamino)cyclohexane
    Yuan, XJ
    Li, YZ
    Liu, YJ
    Tian, YQ
    You, XZ
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 : O640 - O641
  • [5] (1R,2R)-1,2-Diphenyl-1,2-bis(1H-tetrazol-1-yl)ethane
    Werner, Franz
    Mereiter, Kurt
    Tokuno, Kenji
    Inagaki, Yuki
    Hasegawa, Miki
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2726 - U536
  • [6] Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate
    Ganesh, K. Ravi
    Pachore, Sharad S.
    Pratap, T. V.
    Umesh, K.
    Rao, M. V. Basaveswara
    Murthy, C.
    Babu, M. Suresh
    SYNTHETIC COMMUNICATIONS, 2015, 45 (23) : 2676 - 2682
  • [7] Enantioselective synthesis of (-)-(1R,2R)-1,2-dihydrochrysene-1,2-diol
    Lorentzen, Marianne
    Sydnes, Magne O.
    Jorgensen, Kare B.
    TETRAHEDRON, 2014, 70 (47) : 9041 - 9051
  • [8] (1R,2R)-N,N′-Bis(2-pyridylmethylene)cyclohexane-1,2-diamine
    Liu, Bo
    Zhang, Ming-Jie
    Cui, Jin
    Zhu, Jie
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O5359 - O5360
  • [9] (1R,2R)-(+)-1,2-Diphenylethylenediamine
    Jones, MD
    Paz, FAA
    Davies, JE
    Johnson, BFG
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O455 - O457
  • [10] rac-(1R,2R,4S)-1,2-Dibromo-4-[(1R)-1,2-dibromoethyl]cyclohexane
    Koeppen, Robert
    Koch, Matthias
    Emmerling, Franziska
    Nehls, Irene
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O3318 - U1985
12345