Pd-Catalyzed Diastereo- and Enantioselective [3+2]-Cycloaddition Reaction of Vinyl Epoxide with Nitroalkenes

被引:43
|
作者
Wu, Wen-Qiong [1 ]
Ding, Chang-Hua [2 ]
Hou, Xue-Long [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
vinyl epoxide; nitroalkene; palladium; asymmetric catalysis; 3+2] cycloaddition; ASYMMETRIC CYCLOADDITION REACTIONS; SATURATED OXYGEN HETEROCYCLES; ACTIVATED OLEFINS; HECK REACTION; CASCADE REACTIONS; LIGANDS; TETRAHYDROFURANS; VINYLAZIRIDINES; CYCLOPROPANES; DERIVATIVES;
D O I
10.1055/s-0031-1290525
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diastereoselective and enantioselective [3+2]-cycloaddition reaction of vinyl epoxide and nitroalkenes has been developed using Pd/1,1'-ferrocene-P, N-ligand, providing substituted tetrahydrofurans in high yields and with high diastereo- and enantioselectivities.
引用
收藏
页码:1035 / 1038
页数:4
相关论文
共 50 条
  • [31] Metal-Free Diastereo- and Enantioselective Dearomative Formal [3+2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters
    Lavios, Adrian
    Sanz-Marco, Amparo
    Vila, Carlos
    Carmen Munoz, M.
    Pedro, Jose R.
    Blay, Gonzalo
    [J]. ORGANIC LETTERS, 2022, 24 (11) : 2149 - 2154
  • [32] Cinchona Alkaloid-Derived Thiourea-Catalyzed Diastereo- and Enantioselective [3+2]Cycloaddition Reaction of Isocyanoacetates to Isatins: A Facile Access to Optically Active Spirooxindole Oxazolines
    Zhao, Mei-Xin
    Zhou, Hao
    Tang, Wen-Hao
    Qu, Wei-Song
    Shi, Min
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1277 - 1283
  • [33] Diastereo- and Enantioselective Aza-MBH-Type Reaction of Nitroalkenes to N-Tosylimines Catalyzed by Bifunctional Organocatalysts
    Wang, Xiao
    Chen, Yong-Fei
    Niu, Liang-Feng
    Xu, Peng-Fei
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3310 - 3313
  • [34] Palladium-Catalyzed [3+2] Cycloaddition of Vinylaziridine and Indane-1,3-diones: Diastereo- and Enantioselective Access to Spiro-Pyrrolidines
    Vetica, Fabrizio
    Bailey, Stephen J.
    Kumar, Mukesh
    Mahajan, Suruchi
    Rissanen, Kari
    von Essen, Carolina
    Enders, Dieter
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (14): : 2038 - 2044
  • [35] Transmetalation as Key Step in the Diastereo- and Enantioselective Synergistic Cu/Pd-Catalyzed Allylboration of Alkynes with Racemic Allylic Carbonates
    Mateos, Jaime
    Fuentes-Vara, Noelia
    Fra, Laura
    Rivera-Chao, Eva
    Vazquez-Galinanes, Nuria
    Chaves-Pouso, Andrea
    Fananas-Mastral, Martin
    [J]. ORGANOMETALLICS, 2020, 39 (05) : 740 - 745
  • [36] Bifunctional Phase-Transfer Catalysts Catalyzed Diastereo- and Enantioselective Aza-Henry Reaction of β,γ-Unsaturated Nitroalkenes With Amidosulfones
    Lu, Ning
    Bai, Fuquan
    Fang, Yanhong
    Wei, Zhonglin
    Cao, Jungang
    Liang, Dapeng
    Lin, Yingjie
    Duan, Haifeng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) : 4111 - 4116
  • [37] Vinyl-aziridines and cyclopropanes in Pd-catalyzed (3+2)-cycloaddition reactions with cyclic N-sulfonyl imines
    Spielmann, Kim
    Tosi, Eleonora
    Lebrun, Aurelien
    Niel, Gilles
    van der Lee, Arie
    de Figueiredo, Renata Marcia
    Campagne, Jean-Marc
    [J]. TETRAHEDRON, 2018, 74 (45) : 6497 - 6511
  • [38] New chiral ferrocenyl P,S-ligands for highly diastereo- and enantioselective Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
    Han, Mei-Ling
    Wang, Dao-Yong
    Zeng, Pei-Wei
    Zheng, Zhuo
    Hu, Xiang-Ping
    [J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (3-4) : 306 - 312
  • [39] Chiral squaramide-catalyzed highly diastereo- and enantioselective direct Michael addition of nitroalkanes to nitroalkenes
    Yang, Wen
    Du, Da-Ming
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (47) : 12706 - 12708
  • [40] Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3+2] cycloaddition reaction
    Hu, Haiwen
    Yu, Shuxian
    Zhu, Linglong
    Zhou, Lingxiu
    Zhong, Weihui
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (02) : 752 - 760