Transfer of Chirality in the Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of 3-Acyloxy-1,4-enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes

被引：43
作者：
Shu, Xing-zhong [1 ]
Schienebeck, Casi M. [1 ]
Song, Wangze [1 ]
Guzei, Ilia A. [2 ]
Tang, Weiping [1 ,2 ]
机构：
[1] Univ Wisconsin, Sch Pharm, Madison, WI 53705 USA
[2] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 51期
关键词：
catalysis; enynes; polycyclic compounds; rhodium; stereospecific reactions; DIELS-ALDER REACTION; 7-MEMBERED RINGS; PROPARGYLIC ESTERS; RAUTENSTRAUCH REARRANGEMENT; ENE-VINYLCYCLOPROPANES; ALLYLIC ETHERIFICATION; ASYMMETRIC CATALYSIS; METAL; MECHANISM; SELECTIVITY;
D O I：
10.1002/anie.201306919
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：13601 / 13605
页数：5
相关论文
共 73 条
  • [1] Alonso I., 2011, ANGEW CHEM, V123, P11698
  • [2] Enantioselective Gold(I)-Catalyzed Intramolecular (4+3) Cycloadditions of Allenedienes
    Alonso, Isaac
    Faustino, Helio
    Lopez, Fernando
    Mascarenas, Jose L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11496 - 11500
  • [3] [Anonymous], 2008, ANGEW CHEM
  • [4] [Anonymous], 2008, ANGEW CHEM
  • [5] The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings
    Battiste, MA
    Pelphrey, PM
    Wrightthl, DL
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) : 3438 - 3447
  • [6] A fresh look at natural tropolonoids
    Bentley, Ronald
    [J]. NATURAL PRODUCT REPORTS, 2008, 25 (01) : 118 - 138
  • [7] 1,5-α-D-Mannoseptanosides, Ring-Size Isomers That Are Impervious to α-Mannosidase-Catalyzed Hydrolysis
    Boone, Matthew A.
    McDonald, Frank E.
    Lichter, Joseph
    Lutz, Stefan
    Cao, Rui
    Hardcastle, Kenneth I.
    [J]. ORGANIC LETTERS, 2009, 11 (04) : 851 - 854
  • [8] Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions
    Burns, Noah Z.
    Witten, Michael R.
    Jacobsen, Eric N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) : 14578 - 14581
  • [9] Seven-membered rings by cyclization at transition metals:: [4+3], [3+2+2], [5+2]
    Butenschoen, Holger
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (29) : 5287 - 5290
  • [10] Evans P. A., 2006, ANGEW CHEM, V118, P5092
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