Tandem Nazarov cyclization-Michael addition sequence catalyzed by an Ir(III) complex

被引:85
作者
Janka, M
He, W
Haedicke, IE
Fronczek, FR
Frontier, AJ [1 ]
Eisenberg, R
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[2] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
关键词
D O I
10.1021/ja058772o
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first examples of a tandem Nazarov cyclization/Michael addition process are described. The sequence is efficiently catalyzed by Ir[Me(CO)(dppe)(DIB)]2+ and occurs with high diastereoselectivity, creating three contiguous stereocenters. The mechanistic factors controlling the reactivity and diastereoselectivity are discussed. Copyright © 2006 American Chemical Society.
引用
收藏
页码:5312 / 5313
页数:2
相关论文
共 27 条
[1]   Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes [J].
Aggarwal, VK ;
Beffield, AJ .
ORGANIC LETTERS, 2003, 5 (26) :5075-5078
[2]   Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].
Barnes, DM ;
Ji, JG ;
Fickes, MG ;
Fitzgerald, MA ;
King, SA ;
Morton, HE ;
Plagge, FA ;
Preskill, M ;
Wagaw, SH ;
Wittenberger, SJ ;
Zhang, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105
[3]   The palladium(II)-catalyzed Nazarov reaction [J].
Bee, C ;
Leclerc, E ;
Tius, MA .
ORGANIC LETTERS, 2003, 5 (26) :4927-4930
[4]  
CODA AC, 1984, GAZZ CHIM ITAL, V114, P417
[5]   Ionic and covalent copper(II)-based catalysts for Michael additions.: The mechanism [J].
Comelles, J ;
Moreno-Mañas, M ;
Pérez, E ;
Roglans, A ;
Sebastián, RM ;
Vallribera, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6834-6842
[6]   COPPER(II) IN ORGANIC-SYNTHESIS .8. ENANTIOSELECTIVE MICHAEL REACTIONS WITH CHIRAL COPPER(II) COMPLEXES AS CATALYSTS [J].
DESIMONI, G ;
QUADRELLI, P ;
RIGHETTI, PP .
TETRAHEDRON, 1990, 46 (08) :2927-2934
[7]   Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].
Evans, DA ;
Seidel, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9958-9959
[8]   Ni(II) Tol-BINAP-catalyzed enantioselective Michael reactions of β-ketoesters and unsaturated N-acylthiazolidinethiones [J].
Evans, DA ;
Thomson, RJ ;
Franco, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10816-10817
[9]   Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].
Hamashima, Y ;
Hotta, D ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241
[10]   Polarizing the Nazarov Cyclization: Efficient catalysis under mild conditions (vol 125, pg 14278, 2003) [J].
He, W ;
Sun, XF ;
Frontier, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10493-10493