Aza-nazarov reaction and the role of superelectrophiles

被引:88
作者
Klumpp, Douglas A. [1 ]
Zhang, Yiliang
O'Connor, Matthew J.
Esteves, Pierre M.
de Almeida, Leonardo S.
机构
[1] No Illinois Univ, Dept Chem, De Kalb, IL 60115 USA
[2] Univ Fed Rio de Janeiro, Inst Quim, BR-21949900 Rio De Janeiro, RJ, Brazil
关键词
D O I
10.1021/ol0711570
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The superacid-catalyzed reactions of N-acyliminium ion salts have been studied. The new conversions are remarkably similar to the Nazarov reaction and dicationic superelectrophilic species are thought to be involved. Experimental studies show that the cyclizations may be used to prepare varied heterocyclic products, while theoretical studies show that formation of the superelectrophiles can lead to very favorable reaction energetics.
引用
收藏
页码:3085 / 3088
页数:4
相关论文
共 21 条
[1]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[2]   Substituted 3-hydroxypyrroles from 1-azapenta-1,4-dien-3-ones:: The aza-Nazarov reaction -: Synthesis and quantum chemical calculations [J].
Dieker, Juergen ;
Froehlich, Roland ;
Wuerthwein, Ernst-Ulrich .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (23) :5339-5356
[3]  
Frisch M.J., 2004, Gaussian 03
[4]  
Revision C.02
[5]   The Nazarov cyclization in organic synthesis. Recent advances [J].
Frontier, AJ ;
Collison, C .
TETRAHEDRON, 2005, 61 (32) :7577-7606
[6]  
Habermas K.L., 1994, ORG REACTIONS, V45, P1
[7]   Polarizing the Nazarov cyclization: Efficient catalysis under mild conditions [J].
He, W ;
Sun, XF ;
Frontier, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14278-14279
[8]   Cyclizations of N-acyliminium ions [J].
Maryanoff, BE ;
Zhang, HC ;
Cohen, JH ;
Turchi, IJ ;
Maryanoff, CA .
CHEMICAL REVIEWS, 2004, 104 (03) :1431-1628
[9]   Generation of N-acyliminium ions via intramolecular conjugate addition reactions:: A strategy for the total synthesis of nakadomarin A [J].
Nilson, Mark G. ;
Funk, Raymond L. .
ORGANIC LETTERS, 2006, 8 (17) :3833-3836
[10]  
Olah G. A., 1985, Superacids