Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers

被引：51
作者：
Istrate, Florin M. [1 ]
Gagosz, Fabien [1 ]
机构：
[1] Ecole Polytech, CNRS, UMR 7652, Dept Chim, F-91128 Palaiseau, France
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷
关键词：
Claisen rearrangement; furans; gold-catalysis; quaternary centers; HIGHLY SUBSTITUTED FURANS; PALLADIUM-CATALYZED CYCLOISOMERIZATION; EFFICIENT SYNTHESIS; FURAN-2-ACETIC ESTERS; GENERAL-SYNTHESIS; C-C; GOLD; CYCLIZATION; (Z)-2-EN-4-YN-1-OLS; KETONES;
D O I：
10.3762/bjoc.7.100
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of ynenyl allyl ethers were rearranged into polysubstituted furans in the presence of a gold(I) catalyst. It is proposed that the transformation involves a Claisen-type rearrangement that allows the efficient creation of quaternary centers under mild experimental conditions.
引用
收藏
页码：878 / 885
页数：8
相关论文
共 68 条
[1]   An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols [J].
Aponick, Aaron ;
Li, Chuan-Ying ;
Malinge, Jeremy ;
Marques, Emerson Finco .
ORGANIC LETTERS, 2009, 11 (20) :4624-4627
[2]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[3]   Gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes featuring tandem cyclization and [3,3]-sigmatropic rearrangement [J].
Bae, Hyo J. ;
Baskar, Baburaj ;
An, Sang E. ;
Cheong, Jae Y. ;
Thangadurai, Daniel T. ;
Hwang, In-Chul ;
Rhee, Young H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2263-2266
[4]   Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: Pinacol-terminated vs claisen-terminated cyclization cascades [J].
Baskar, Baburaj ;
Bae, Hyo J. ;
An, Sang E. ;
Cheong, Jae Y. ;
Rhee, Young H. ;
Duschek, Alexander ;
Kirsch, Stefan F. .
ORGANIC LETTERS, 2008, 10 (12) :2605-2607
[5]   Gold-catalyzed cycloisomerization of alk-4-yn-1-ones [J].
Belting, Volker ;
Krause, Norbert .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (06) :1221-1225
[6]   Gold(I)-Catalyzed Tandem Rearrangement-Nucleophilic Substitution of α-Acetoxy Alkynyl Oxiranes or Aziridines: Efficient Approach to Furans and Pyrroles [J].
Blanc, Aurelien ;
Alix, Aurelien ;
Weibel, Jean-Marc ;
Pale, Patrick .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (09) :1644-1647
[7]   Mechanistic Studies and Improvement of Coinage Metal-Catalyzed Transformation of Alkynyloxiranes to Furans: An Alcohol Addition-Cyclization-Elimination Cascade [J].
Blanc, Aurelien ;
Tenbrink, Katharina ;
Weibel, Jean-Marc ;
Pale, Patrick .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5342-5348
[8]   Gold(I)-Catalyzed Rearrangement of Propargyl Benzyl Ethers: A Practical Method for the Generation and in Situ Transformation of Substituted Allenes [J].
Bolte, Benoit ;
Odabachian, Yann ;
Gagosz, Fabien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7294-+
[9]   Developments in furan syntheses [J].
Brown, RCD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852
[10]   Heterocycles via cyclization of alkynes promoted by organopalladium complexes [J].
Cacchi, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :42-64
1234567