Asymmetric aza-Diels-Alder reaction of Danishefsky's diene with imines in a chiral reaction medium

被引:33
|
作者
Pegot, Bruce [1 ]
Van Buu, Olivier Nguyen [1 ]
Gori, Didier [1 ]
Vo-Thanh, Giang [1 ]
机构
[1] Univ Paris 11, Lab Chim Procedes & Subst Nat, ICMMO, CNRS,UMR 8182, F-91405 Orsay, France
关键词
D O I
10.1186/1860-5397-2-18
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric aza-Diels-Alder reaction of chiral imines with Danishefsky's diene in chiral ionic liquids provides the corresponding cycloadduct with moderate to high diastereoselectivity. The reaction has proved to perform better at room temperature in ionic liquids without either Lewis acid catalyst or organic solvent. Chiral ionic liquids are recycled while their efficiency is preserved.
引用
收藏
页数:5
相关论文
共 50 条
  • [41] Aza-Diels-Alder Reaction: An Efficient Approach for Construction of Heterocycles
    Sarmah, Manas M.
    Prajapati, Dipak
    CURRENT ORGANIC CHEMISTRY, 2014, 18 (12) : 1586 - 1620
  • [42] Bismuth(III) chloride catalyzed aza-Diels-Alder reaction
    Reddy, BVS
    Srinivas, R
    Yadav, JS
    Ramalingam, T
    SYNTHETIC COMMUNICATIONS, 2001, 31 (07) : 1075 - 1080
  • [43] Cobalt(III) Porphyrin Catalyzed Aza-Diels-Alder Reaction
    Wakabayashi, Ryota
    Kurahashi, Takuya
    Matsubara, Seijiro
    ORGANIC LETTERS, 2012, 14 (18) : 4794 - 4797
  • [44] Is the pericyclic transition structure of aza-Diels-Alder reaction aromatic?
    Benallou, Abdelilah
    Kerraj, Said
    El Abdallaoui, Habib El Alaoui
    Garmes, Hocine
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2019, 91 : 119 - 129
  • [45] The use of nonactivated iminodienophiles in the stereoselective aza-Diels-Alder reaction
    Trifonova, A
    Andersson, PG
    TETRAHEDRON-ASYMMETRY, 2004, 15 (03) : 445 - 452
  • [46] The Aryne aza-Diels-Alder Reaction: Flexible Syntheses of Isoquinolines
    Castillo, Juan-Carlos
    Quiroga, Jairo
    Abonia, Rodrigo
    Rodriguez, Jean
    Coquerel, Yoann
    ORGANIC LETTERS, 2015, 17 (13) : 3374 - 3377
  • [47] Asymmetric Hetero-Diels-Alder Reaction of Danishefsky's Diene with α-Ketoesters and Isatins Catalyzed by a Chiral N,N′-Dioxide/Magnesium(II) Complex
    Zheng, Jianfeng
    Lin, Lili
    Fu, Kai
    Zhang, Yulong
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (44) : 14493 - 14498
  • [48] An asymmetric normal-electron-demand aza-Diels-Alder reaction via trienamine catalysis
    Liu, Jing-Xin
    Zhou, Qing-Qing
    Deng, Jin-Gen
    Chen, Ying-Chun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (47) : 8175 - 8178
  • [49] endo-1-Phenylborneol as a novel, alternative chiral auxiliary for the aza-Diels-Alder reaction
    Bassani, Marco
    Scarso, Alessandro
    Drago, Maria
    Zambon, Alfonso
    Fabris, Fabrizio
    TETRAHEDRON LETTERS, 2020, 61 (31)
  • [50] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity
    Akiyama, T
    Tamura, Y
    Itoh, J
    Morita, H
    Fuchibe, K
    SYNLETT, 2006, (01) : 141 - 143