AuCl-catalyzed synthesis of benzyl-protected substituted phenols: A formal [3+3] approach

被引:34
作者
Huang, Xiaogen [1 ]
Zhang, Liming [1 ]
机构
[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA
关键词
D O I
10.1021/ol7021356
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A AuCl-catalyzed synthesis of highly substituted, benzyl-protected phenols is developed. This reaction unites enal/enones and benzyl allenyl ether in a [3+3] fashion in two steps, allowing flexibility in phenol synthesis and excellent control of substitution at the benzene ring.
引用
收藏
页码:4627 / 4630
页数:4
相关论文
共 17 条
[1]   Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615
[2]   CHEMISTRY OF CYCLOPROPANOLS [J].
DEPUY, CH .
ACCOUNTS OF CHEMICAL RESEARCH, 1968, 1 (02) :33-&
[3]   One-pot synthesis of functionalized carbacycles by formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles [J].
Feist, Holger ;
Langer, Peter .
SYNTHESIS-STUTTGART, 2007, (03) :327-347
[4]   Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].
Fuerstner, Alois ;
Davies, Paul W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449
[5]   Relativistic effects in homogeneous gold catalysis [J].
Gorin, David J. ;
Toste, F. Dean .
NATURE, 2007, 446 (7134) :395-403
[6]   Gold-catalyzed organic reactions [J].
Hashmi, A. Stephen K. .
CHEMICAL REVIEWS, 2007, 107 (07) :3180-3211
[7]   Gold catalysis:: Oxepines from γ-alkynylfurans [J].
Hashmi, A. Stephen K. ;
Kurpejovic, Elzen ;
Woelfle, Michael ;
Frey, Wolfgang ;
Bats, Jan W. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) :1743-1750
[8]   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
[9]   Highly selective gold-catalyzed arene synthesis [J].
Hashmi, ASK ;
Frost, TM ;
Bats, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11553-11554
[10]   Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: Gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center [J].
Huang, Xiaogen ;
Zhang, Liming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (20) :6398-+