Gold-Catalyzed 1,3-Acyloxy Migration/5-exo-dig Cyclization/1,5-Acyl Migration of Diynyl Esters

被引：85
|
作者：
Leboeuf, David [1 ]
Simonneau, Antoine [1 ]
Aubert, Corinne [1 ]
Malacria, Max [1 ]
Gandon, Vincent [2 ]
Fensterbank, Louis [1 ]
机构：
[1] UPMC Paris 06, IPCM UMR CNRS 7201, F-75252 Paris 05, France
[2] Univ Paris 11, UMR CNRS 8182, F-91405 Orsay, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 30期
关键词：
cycloisomerization; diynes; gold; homogeneous catalysis; CYCLOISOMERIZATION; ACCESS; ACTIVATION; ENYNES;
D O I：
10.1002/anie.201101179
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Working three shifts: Polyconjugated δ-diketones are formed stereoselectively in high yields by the gold-catalyzed rearrangement of 1,6-diyn-3-yl esters. This cascade involves a 1,3-sigmatropic acyloxy shift, a 5-exo-dig cyclization of the resulting allenyne, and an unprecedented 1,5-sigmatropic shift of an acyl fragment. The usefulness of the products was shown by an efficient acid-catalyzed transformation into a complex polycyclic framework. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：6868 / 6871
页数：4
相关论文
共 50 条
  • [21] Stereoselective Synthesis of α-Trifluoromethyl Enones by AuI/CuI-Co-Catalyzed Tandem 1,3-Acyloxy Migration/Trifluoromethylation Reaction of Propargyl Acetates
    Ji, Yun-Long
    Lin, Jin-Hong
    Xiao, Ji-Chang
    Gu, Yu-Cheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (35) : 7948 - 7954
  • [22] Tandem Rh(<sc>ii</sc>)-catalyzed 1,3-acyloxy migration/intermolecular [2+2] cycloaddition of electron-deficient propargylic esters with alkenes and alkynes
    Xu, Zurong
    Zhu, Dong
    Wu, Rui
    Zhu, Shifa
    CHEMICAL SCIENCE, 2024, 16 (01) : 205 - 210
  • [23] Au-Catalyzed 1,3-Acyloxy Migration/Cyclization Cascade: A Direct Strategy toward the Synthesis of Functionalized Abietane-Type Diterpenes (vol 2, pg 2669, 2020)
    Zhang, T. L.
    CCS CHEMISTRY, 2022, 4 (12): : 3904 - 3904
  • [24] Gold-Catalyzed Tandem 1,3-Migration/Double Cyclopropanation of 1-Ene-4,n-diyne Esters to Tetracyclodecene and Tetracycloundecene Derivatives
    Chen, Cuili
    Zou, Yongzhen
    Chen, Xianxiao
    Zhang, Xiaoxiang
    Rao, Weidong
    Chan, Philip Wai Hong
    ORGANIC LETTERS, 2016, 18 (18) : 4730 - 4733
  • [25] The Effect of HSAB on Stereoselectivity: Copper- and Gold-Catalyzed 1,3-Phosphatyloxy and 1,3-Halogen Migration Relay to 1,3-Dienes
    Jiang, Jingxing
    Hou, Cheng
    Zhang, Shidong
    Luan, Zihong
    Zhao, Cunyuan
    Ke, Zhuofeng
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1661 - 1671
  • [26] A DFT study on the mechanism of Rh-catalyzed competitive 1,2-versus 1,3-acyloxy migration followed by [5+1] and [4+1] cycloadditions of 1,4-enynes with CO
    Coskun, Dilek
    Tuzun, Nurcan S.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 851 : 97 - 103
  • [27] Metal-free entry to phosphonylated isoindoles by a cascade of 5-exo-dig cyclization, a [1,3]-alkyl shift, and aromatization under microwave heating
    Dieltiens, Nicolai
    Stevens, Christian V.
    ORGANIC LETTERS, 2007, 9 (03) : 465 - 468
  • [28] Silver(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Mannich-type Addition/Elimination of the Sulfonyl Group of N-Sulfonylhydrazone-propargylic Esters to 5,6-Dihydropyridazin-4-one Derivatives
    Zhang, Zhen
    Shi, Min
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (12) : 3654 - 3658
  • [29] Gold-Catalyzed Formal 1,6-Acyloxy Migration Leading to 3,4-Disubstituted Pyrrolidin-2-ones
    Hashmi, A. Stephen K.
    Yang, Weibo
    Yu, Yang
    Hansmann, Max M.
    Rudolph, Matthias
    Rominger, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (04) : 1329 - 1332
  • [30] A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles
    Sun, Yin-Wei
    Tang, Xiang-Ying
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2015, 51 (73) : 13937 - 13940
12345