Gold(I)-catalyzed conia-ene reaction of β-ketoesters with alkynes

被引:395
作者
Kennedy-Smith, JJ [1 ]
Staben, ST [1 ]
Toste, FD [1 ]
机构
[1] Univ Calif Berkeley, Ctr New Direct Organ Synth, Dept Chem, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja049487s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The intramolecular addition of β-ketoesters to unactivated alkynes under neutral conditions and at room temperature is described. The method employs triphenylphosphinegold(I) cation as a catalyst for the formation of exo-methylenecycloalkanes. Both monocyclic and bicyclic cyclopentanes and cyclohexanes can be formed in excellent yields and with good diastereoselectivity. Copyright © 2004 American Chemical Society.
引用
收藏
页码:4526 / 4527
页数:2
相关论文
共 36 条
[11]   Stoichiometric and catalytic reactions of gold utilizing ionic liquids [J].
Deetlefs, M ;
Raubenheimer, HG ;
Esterhuysen, MW .
CATALYSIS TODAY, 2002, 72 (1-2) :29-41
[12]   Stereoselective formation of quaternary carbon centers and related functions [J].
Denissova, I ;
Barriault, L .
TETRAHEDRON, 2003, 59 (51) :10105-10146
[13]  
Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
[14]  
2-A
[15]   Gold(III) chloride-catalyzed addition reactions of electron-rich arenes to methyl vinyl ketone [J].
Dyker, G ;
Muth, E ;
Hashmi, ASK ;
Ding, L .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (11) :1247-1252
[16]   EFFECTIVE TRANSFORMATION OF UNACTIVATED ALKYNES INTO KETONES OR ACETALS BY MEANS OF AU(III) CATALYST [J].
FUKUDA, Y ;
UTIMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3729-3731
[17]  
FUKUDA Y, 1991, SYNTHESIS-STUTTGART, P975
[18]   GOLD(III)-CATALYZED ONE-POT SYNTHESIS OF ISOXAZOLES FROM TERMINAL ALKYNES AND NITRIC-ACID [J].
GASPARRINI, F ;
GIOVANNOLI, M ;
MISITI, D ;
NATILE, G ;
PALMIERI, G ;
MARESCA, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4401-4402
[19]   Gold catalysis: On the phenol synthesis [J].
Hashmi, ASK ;
Frost, TM ;
Bats, JW .
ORGANIC LETTERS, 2001, 3 (23) :3769-3771
[20]   Homogeneous gold catalysts and alkynes: A successful liaison [J].
Hashmi, ASK .
GOLD BULLETIN, 2003, 36 (01) :3-9