Asymmetric Pd-catalyzed allylic amination of 1,3-diphenylallyl acetate with dipropylamine in ionic and molecular solvents

被引：3
|
作者：
Lyubimov, SE
Davankov, VA
Kucherenko, AS
Zlotin, SG
Zheglov, SV
Gavrilov, KN
Petrovskii, PV
机构：
[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
[2] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[3] SA Esenin Ryazan State Pedag Univ, Ryazan 390000, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2005年 / 54卷 / 11期
关键词：
chiral phosphites; palladium complexes; asymmetric ammination; ionic liquid; catalyst cycles;
D O I：
10.1007/s11172-006-0155-9
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Asymmetric catalytic allylic amination of 1,3-diphenylallyl acetate with dipropylamine in an ionic liquid, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, and in THF and CH2Cl2 in the presence of palladium complexes of P-monodentate phosphite and phosphoramidite derivatives of S-1,1'-bis-2-naphthol was carried Out. This gave a product with ee of up to 65%. The level of asymmetric induction is retained after three catalyst cycles.
引用
收藏
页码：2558 / 2561
页数：4
相关论文
共 50 条
  • [41] Development of Pd-Catalyzed Asymmetric Allylic Alkylation with Low Catalyst Loading for Large-Scale Production of Ethyl (R)-1-Allyl-2-oxocyclohexane-1-carboxylate
    Zhang, Yongda
    White, Jada A. H.
    Chong, Eugene
    Radomkit, Suttipol
    Xu, Yibo
    Liu, Jing
    Lorenz, Jon C.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2023, 27 (07) : 1406 - 1410
  • [42] Pd-Catalyzed Asymmetric Hydroalkylation of 1,3-Dienes: Access to Unnatural α-Amino Acid Derivatives Containing Vicinal Quaternary and Tertiary Stereogenic Centers
    Zhang, Zongpeng
    Xiao, Fan
    Wu, Hui-Min
    Dong, Xiu-Qin
    Wang, Chun-Jiang
    ORGANIC LETTERS, 2020, 22 (02) : 569 - 574
  • [43] Pd-Catalyzed asymmetric [5+2] cycloaddition of vinylethylene carbonates and cyclic imines: access to N-fused 1,3-oxazepines
    Ahn, Hye-In
    Park, Jong-Un
    Xuan, Zi
    Kim, Ju Hyun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (48) : 9826 - 9830
  • [44] Stereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1,3-Asymmetric Induction by Manipulating Mechanistic Pathways
    Babij, Nicholas R.
    McKenna, Grace M.
    Fornwald, Ryan M.
    Wolfe, John P.
    ORGANIC LETTERS, 2014, 16 (12) : 3412 - 3415
  • [45] Access to a Novel Class of Tetracyclic 1,4-Benzodiazepin-5-ones Starting from α-Amino Acids by Pd-Catalyzed Amination/1,3-Dipolar Cycloaddition as the Key Steps
    Basolo, Luca
    Beccalli, Egle M.
    Borsini, Elena
    Broggini, Gianluigi
    Khansaa, Maisaa
    Rigamonti, Micol
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (09) : 1694 - 1703
  • [46] Features of Pd-catalyzed reactions of allylic acetates elimination in racemic cloprostenol methyl ester triacetate and 15-acetate of methyl ester 11-deoxyprostaglandin E1
    Zagitov, Vadim V.
    Khursan, Sergey L.
    Vostrikov, Nikolay S.
    Lobov, Alexander N.
    Petrova, Svetlana F.
    Miftakhov, Mansur S.
    TETRAHEDRON, 2024, 166
  • [47] ortho-silylation of 2,2′-bis(oxazolinyl)-1,1′-bis(diphenylphosphino)ferrocenes and remarkable effect of the silyl groups on the enantio selectivity in Pd-catalyzed asymmetric allylic alkylation
    Lee, S
    Koh, JH
    Park, J
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 637 : 99 - 106
  • [48] A novel tandem Pd-catalyzed intramolecular allylic decarboxylative coupling and "diradical conjugated 1,3-dien-5-yne cycloaromatization": An unusual ortho-selectivity in the cycloaromatization and the mechanistic implications
    Tummanapalli, Satyanarayana
    Vangapandu, Dhanunjaya Naidu
    Muthuraman, Parthasarathy
    Kambampati, Sanjeeva
    Shanmugavel, Gnanakalai
    TETRAHEDRON LETTERS, 2017, 58 (32) : 3125 - 3131
  • [49] Pd-catalyzed asymmetric allylic alkylation of 3-acetoxy-N-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine -: Preparation of key intermediates for natural product synthesis
    Schleich, S
    Helmchen, G
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (10) : 2515 - 2521
  • [50] Molecular structure of 1,3-disubstituted pi-allyl palladium(II) complexes with a chiral diphosphine: The intermediate of palladium-catalyzed asymmetric allylic alkylation
    Yamaguchi, M
    Yabuki, M
    Yamagishi, T
    Sakai, K
    Tsubomura, T
    CHEMISTRY LETTERS, 1996, (03) : 241 - 242
12345