A new catalytic conjugate addition/aldol strategy that avoids preformed metalated nucleophiles

被引:64
作者
Subburaj, K [1 ]
Montgomery, J [1 ]
机构
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
关键词
D O I
10.1021/ja0362048
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new conjugate addition/aldol strategy has been developed. Unlike conventional procedures that require metalation of the nucleophilic species, the procedure allows the direct coupling of aryl iodides, aldehydes, and acrylates in a nickel-catalyzed, organozinc-promoted process. Copyright © 2003 American Chemical Society.
引用
收藏
页码:11210 / 11211
页数:2
相关论文
共 27 条
[1]   Oxidative addition of aryl halides to transient anionic sigma-aryl-palladium(0) intermediates - Application to palladium-catalyzed reductive coupling of aryl halides [J].
Amatore, C ;
Carre, E ;
Jutand, A ;
Tanaka, H ;
Ren, QH ;
Torii, S .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (08) :957-966
[2]   Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction [J].
Arnold, LA ;
Naasz, R ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7244-7254
[3]   Tandem radical addition-aldol condensations:: evidence for the formation of zinc enolates in diethylzinc mediated radical additions to N-enoyloxazolidinones [J].
Bazin, S ;
Feray, L ;
Siri, D ;
Naubron, JV ;
Bertrand, MP .
CHEMICAL COMMUNICATIONS, 2002, (21) :2506-2507
[4]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[5]   A general synthetic entry to Strychnos alkaloids of the curan type via a common 3a-(2-nitrophenyl)hexahydroindol-4-one intermediate. Total syntheses of (+/-)- and (-)-tubifolidine, (+/-)-akuammicine, (+/-)-19,20-dihydroakuammicine, (+/-)-norfluorocurarine, (+/-)-echitamidine, and (+/-)-20-epilochneridine [J].
Bonjoch, J ;
Sole, D ;
GarciaRubio, S ;
Bosch, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (31) :7230-7240
[6]   Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].
Cauble, DF ;
Gipson, JD ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111
[7]  
Chapdelaine M.J., 1990, ORG REACT, V38, P225
[8]   NEW SEQUENTIAL CARBON-CARBON BOND FORMING REACTIONS - A SAMARIUM(II) IODIDE MEDIATED VINYLOGOUS BARBIER REACTION FOLLOWED BY AN ALDOL REACTION [J].
CURRAN, DP ;
WOLIN, RL .
SYNLETT, 1991, (05) :317-318
[9]   Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents [J].
Feringa, BL ;
Pineschi, M ;
Arnold, LA ;
Imbos, R ;
de Vries, AHM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2620-2623
[10]   ON THE LEWIS ACIDITY OF NICKEL(0) .10. DIORGANYLMAGNESIUM COMPLEXES OF NICKEL(0) - (TMEDA)MGCH3(MU-CH3)NI(C2H4)2 [J].
KASCHUBE, W ;
PORSCHKE, KR ;
ANGERMUND, K ;
KRUGER, C ;
WILKE, G .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (11) :1921-1929