A highly efficient preparative method of α-ylidene-β-diketones via AuIII-catalyzed acyl migration of propargylic esters

被引：172
作者：
Wang, Shaozhong [1 ]
Zhang, Liming [1 ]
机构：
[1] Univ Nevada, Dept Chem 216, Reno, NV 89557 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 26期
关键词：
D O I：
10.1021/ja062777j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly efficient synthesis of α-alkylidene or benzylidene-β-diketones from readily available propargylic esters has been developed. The proposed key transformation is a novel intramolecular acyl migration to nucleophilic AuIII-C(sp2) bonds. Noteworthy features of this method are its efficiency and stereoselectivity. The yields of this reaction were mostly close to quantitative, and high to excellent stereoselectivities were observed in the cases of dienyl β-diketones. Copyright © 2006 American Chemical Society.
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页码：8414 / 8415
页数：2
相关论文
共 21 条
[1]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[2]   Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].
Buzas, A ;
Gagosz, F .
ORGANIC LETTERS, 2006, 8 (03) :515-518
[3]   COMPLEXES OF GOLD(III) WITH MONONEGATIVE BIDENTATE N,O-LIGANDS [J].
DAR, A ;
MOSS, K ;
COTTRILL, SM ;
PARISH, RV ;
MCAULIFFE, CA ;
PRITCHARD, RG ;
BEAGLEY, B ;
SANDBANK, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (12) :1907-1913
[4]  
Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
[5]  
2-A
[6]   Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes [J].
Echavarren, AM ;
Nevado, C .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :431-436
[7]   Gold catalysis: The benefits of N and N,O ligands [J].
Hashmi, ASK ;
Weyrauch, JP ;
Rudolph, M ;
Kurpejovic, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) :6545-6547
[8]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO
[9]  
2-F
[10]   Homogeneous gold catalysts and alkynes: A successful liaison [J].
Hashmi, ASK .
GOLD BULLETIN, 2003, 36 (01) :3-9
123