AuCl3 catalyzed [3+2+1] cycloaddition: first use of aldehyde as a carbon monoxide-like one carbon synthon for triple C-C coupling

被引:9
作者
Gayen, Krishnanka S. [1 ]
Maiti, Dilip K. [1 ]
机构
[1] Univ Calcutta, Univ Coll Sci, Dept Chem, Kolkata 700009, India
关键词
H BOND ACTIVATION; X=Y-ZH SYSTEMS; CASCADE CYCLIZATION; ALKALOIDS; FUNCTIONALIZATION; CONSTRUCTION; PERSPECTIVE; DERIVATIVES; ANALOGS; ESTERS;
D O I
10.1039/c3ra47093h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new [3 + 2 + 1] cycloaddition strategy is demonstrated using an aldehyde, an aldimine of a glycine ester and a terminal triple bond with AuCl3 catalyst. Aldehyde is exploited as the first alternative to the crucial partner CO for triple C-C coupled annulation for the synthesis of novel fused-tricyclic heterocycles.
引用
收藏
页码:10204 / 10207
页数:4
相关论文
共 44 条
[1]  
Aksanova L. A., 1970, SYNTHESIS OF SOME NE, V6, P1478
[2]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .5. INTRAMOLECULAR CYCLO-ADDITIONS OF IMINES OF ALPHA-AMINO-ACID ESTERS [J].
ARMSTRONG, P ;
GRIGG, R ;
JORDAN, MW ;
MALONE, JF .
TETRAHEDRON, 1985, 41 (17) :3547-3558
[3]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[4]   C-H Bond Activation in Transition Metal Species from a Computational Perspective [J].
Balcells, David ;
Clot, Eric ;
Eisenstein, Odile .
CHEMICAL REVIEWS, 2010, 110 (02) :749-823
[5]  
Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]
[6]   Gold-Catalyzed Dehydrative Transformations of Unsaturated Alcohols [J].
Biannic, Berenger ;
Aponick, Aaron .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (33) :6605-6617
[7]   Gold-mediated C-H bond functionalisation [J].
Boorman, Tanya C. ;
Larrosa, Igor .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1910-1925
[8]   [3+2+1] cycloaddition involving alkynes, CO and bridging vinyliminium ligands in diiron complexes: a dinuclear version of the Dotz reaction? [J].
Busetto, Luigi ;
Marchetti, Fabio ;
Mazzoni, Rita ;
Salmi, Mauro ;
Zacchini, Stefano ;
Zanotti, Valerio .
CHEMICAL COMMUNICATIONS, 2010, 46 (19) :3327-3329
[9]   1,3-DIPOLAR CYCLOADDITION REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES AND THE FORMAL [3 + 2 + 1] PYRIDINANNULATION OF THE CYCLOADDUCTS [J].
CHAN, KS ;
WULFF, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5229-5236
[10]   Generation of nitrile oxides under nanometer micelles built in neutral aqueous media: Synthesis of novel glycal-based chiral synthons and optically pure 2,8-dioxabicyclo[4.4.0]decene core [J].
Chatterjee, Nirbhik ;
Pandit, Palash ;
Halder, Samiran ;
Patra, Amarendra ;
Maiti, Dilip K. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7775-7778