Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction of Tropones

被引：99
|
作者：
Li, Pingfan [1 ]
Yamamoto, Hisashi [1 ]
机构：
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 46期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
ASYMMETRIC CLAISEN REARRANGEMENT; CHIRAL ORGANOALUMINUM REAGENT; PERFLUOROPHENYL DERIVATIVES; VINYL ETHERS; RING-SYSTEM; ALDOL-TYPE; TRIS(PENTAFLUOROPHENYL)BORON; CYCLOADDITIONS; EFFICIENT; CP-225,917;
D O I：
10.1021/ja908127f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Lewis acid catalyzed inverse-electron-demand Diets-Alder reaction of tropone derivatives was developed. Up to 97% ee was obtained for the chiral dinucleus BINOL-aluminum complex catalyzed reaction between tropones and ketene diethyl acetal to give bicyclo[3.2.2] ring structures, which opens up a unique way of making chiral seven-membered rings.
引用
收藏
页码：16628 / +
页数：3
相关论文
共 50 条
  • [21] Tetrazines in Inverse-Electron-Demand Diels-Alder Cycloadditions and Their Use in Biology
    Mayer, Susanne
    Lang, Kathrin
    SYNTHESIS-STUTTGART, 2017, 49 (04): : 830 - 848
  • [22] Chelated Diborenes and Their Inverse-Electron-Demand Diels-Alder Reactions with Dienes
    Stennett, Tome.
    Mattock, James D.
    Pentecost, Leanne
    Vargas, Alfredo
    Braunschweig, Holger
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (46) : 15276 - 15281
  • [23] Chiral Phosphoric Acid Catalyzed Inverse-Electron-Demand Aza-Diels-Alder Reaction of Isoeugenol Derivatives
    He, Long
    Bekkaye, Mathieu
    Retailleau, Pascal
    Masson, Geraldine
    ORGANIC LETTERS, 2012, 14 (12) : 3158 - 3161
  • [24] Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of 2-Pyrones with Styrenes and Indenes
    Yu, Heng-Bin
    Chen, Yang-Guang
    Tian, Yin
    Xie, Ming-Sheng
    Guo, Hai-Ming
    ACS CATALYSIS, 2024, 14 (11): : 8930 - 8938
  • [25] Organocatalytic Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of Electron-Deficient Dienes and Crotonaldehyde
    Li, Jun-Long
    Kang, Tai-Ran
    Zhou, Si-Li
    Li, Rui
    Wu, Li
    Chen, Ying-Chun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (36) : 6418 - 6420
  • [26] Mechanistic Study of Domino Processes Involving the Bidentate Lewis Acid Catalyzed Inverse Electron-Demand Diels-Alder Reaction
    Strauss, Marcel A.
    Kohrs, Daniel
    Ruhl, Julia
    Wegner, Hermann A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (28) : 3866 - 3873
  • [27] Mechanistic Studies on the Bidentate Lewis Acid Catalyzed Domino Inverse Electron-Demand Diels-Alder/Thiol Transfer Reaction
    Beeck, Sebastian
    Wegner, Hermann A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022,
  • [28] Organocatalytic Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of Pyrrolidone-Dienes with Enals
    Wu, Shu-Xiao
    Gu, Bo-Qi
    Xu, Hui
    Zheng, Xing
    Luo, Xiaoyan
    Deng, Wei-Ping
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) : 4302 - 4313
  • [29] Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of β,γ-Unsaturated Amides through Dienolate Catalysis
    Qin, Jialiang
    Zhang, Yili
    Liu, Cuiting
    Zhou, Jun
    Zhan, Ruoting
    Chen, Weiwen
    Huang, Huicai
    ORGANIC LETTERS, 2019, 21 (18) : 7337 - 7341
  • [30] Towards a bioorthogonal exchange reaction based on an inverse-electron-demand Diels-Alder (iEDDA) cycloaddition
    Van Dyke, Aaron
    Gatazka, Daniel
    Hanania, Mariah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
12345