Gold-Catalyzed Cycloisomerization of Functionalized 1,5-Enynes - An Entry to Polycyclic Framework

被引：25
|
作者：
Pradal, Alexandre [1 ,2 ]
Chen, Qian [1 ,2 ]
Bel, Pierre Faudot Dit [1 ,2 ]
Toullec, Patrick Yves [1 ,2 ]
Michelet, Veronique [1 ,2 ]
机构：
[1] Chim ParisTech, LCF, F-75231 Paris 05, France
[2] CNRS, UMR 7223, F-75231 Paris 05, France
来源：
SYNLETT | 2012年 / 23卷 / 01期
关键词：
gold catalyst; cycloisomerization; 1,5-enynes; atom economy; polycyclization; ACETYLENIC CARBOXYLIC-ACIDS; EFFICIENT ACCESS; HIGHLY EFFICIENT; SELECTIVE CYCLOISOMERIZATION; GOLD(I)-CATALYZED SYNTHESIS; ELECTROPHILIC ACTIVATION; INTERMOLECULAR ADDITION; PLATINUM CATALYSIS; ENYNES; CYCLIZATION;
D O I：
10.1055/s-0031-1289867
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The gold-catalyzed cycloisomerization reactions of variously functionalized 1,5-enynes are presented. The cyclization processes implying aryl-and 1,3-dicarbonyl-substituted skeletons are conducted under mild conditions and lead to cyclic structures obtained according to 6-endo-dig or 5-endo-dig mode depending on the involved nucleophilic partner. Some competitive pathways and trapping of carbocationic intermediates are highlighted.
引用
收藏
页码：74 / 79
页数：6
相关论文
共 50 条
  • [1] DFT Studies on Gold-Catalyzed Cycloisomerization of 1,5-Enynes
    Fan, Ting
    Chen, Xihan
    Sun, Jianwei
    Lin, Zhenyang
    ORGANOMETALLICS, 2012, 31 (11) : 4221 - 4227
  • [2] Gold(I)-catalyzed dehydrogenative cycloisomerization of 1,5-enynes
    Chen, Gen-Qiang
    Fang, Wei
    Wei, Yin
    Tang, Xiang-Ying
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2016, 52 (71) : 10799 - 10802
  • [3] Gold-Catalyzed Enantioselective Ring-Expanding Cycloisomerization of Cyclopropylidene Bearing 1,5-Enynes
    Zheng, Hongchao
    Felix, Ryan J.
    Gagne, Michel R.
    ORGANIC LETTERS, 2014, 16 (08) : 2272 - 2275
  • [4] A DFT-Based Analysis of the Gold-Catalyzed Cycloisomerization of 1-Siloxy 1,5-Enynes to Cyclohexadienes
    Soriano, Elena
    Marco-Contelles, Jose
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14): : 6231 - 6238
  • [5] Gold-Catalyzed Cyclization of Oxo-1,5-enynes
    Huguet, Nuria
    Echavarren, Antonio M.
    SYNLETT, 2012, 23 (01) : 49 - 53
  • [6] Gold-Catalyzed Benzannulation of 3-Alkoxy-1,5-enynes: Access to Functionalized Benzenes
    Li, Guijie
    Liu, Yuanhong
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09): : 2903 - 2909
  • [7] A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes
    Guo, Jia
    Peng, Xiaoshi
    Wang, Xiaoyu
    Xie, Fukai
    Zhang, Xinhang
    Liang, Guoduan
    Sun, Zenghui
    Liu, Yongxiang
    Cheng, Maosheng
    Liu, Yang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (47) : 9147 - 9151
  • [8] Gold-Catalyzed Oxidative Cyclization of 1,5-Enynes Using External Oxidants
    Vasu, Dhananjayan
    Hung, Hsiao-Hua
    Bhunia, Sabyasachi
    Gawade, Sagar Ashok
    Das, Arindam
    Liu, Rai-Shung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (30) : 6911 - 6914
  • [9] A gold-catalyzed unique cycloisomerization of 1,5-enynes: Efficient formation of 1-carboxycyclohexa-1,4-dienes and carboxyarenes
    Wang, Shaozhong
    Zhang, Liming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) : 14274 - 14275
  • [10] Mimicking Polyolefin Carbocyclization Reactions: Gold-Catalyzed Intramolecular Phenoxycyclization of 1,5-Enynes
    Toullec, Patrick Yves
    Blarre, Thomas
    Michelet, Veronique
    ORGANIC LETTERS, 2009, 11 (13) : 2888 - 2891
12345