Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids:: An entry to functionalized γ-lactones

被引:238
作者
Genin, E [1 ]
Toullec, PY [1 ]
Antoniotti, S [1 ]
Brancour, C [1 ]
Genêt, JP [1 ]
Michelet, V [1 ]
机构
[1] ENSCP, Lab Synth Select Organ & Prod Nat, UMR 7573, F-75231 Paris 05, France
关键词
D O I
10.1021/ja056857j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient gold-catalyzed cyclization reaction of various functionalized acetylenic acids is described. The cyclizations are conducted in the presence of Au(I) catalyst in acetonitrile at room temperature in a short reaction time. The reaction conditions are compatible with several functional groups, such as ester, alkene, alkyne, chloro, and free or protected alcohol, and lead to original γ-lactones in good to excellent yields. Copyright © 2006 American Chemical Society.
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收藏
页码:3112 / 3113
页数:2
相关论文
共 53 条
[1]   Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones [J].
Alfonsi, M ;
Arcadi, A ;
Aschi, M ;
Bianchi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2265-2273
[2]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[3]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[4]   Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].
Antoniotti, S ;
Genin, E ;
Michelet, V ;
Genêt, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977
[5]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[6]   Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles [J].
Arcadi, A ;
Bianchi, G ;
Marinelli, F .
SYNTHESIS-STUTTGART, 2004, (04) :610-618
[7]   Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].
Asao, N ;
Nogami, T ;
Lee, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925
[8]  
BALME G, 2002, HDB ORGANOPALLADIUM, P2245
[9]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[10]  
BIANCHI G, 2004, TARGETS HETEROCYCLIC, V8, P82