Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents

被引:123
作者
Lou, Sha [1 ]
Fu, Gregory C. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院;
关键词
RACEMIC ALPHA-BROMOKETONES; SECONDARY ALKYL-HALIDES; ARYLZINC REAGENTS; VINYLATION; ELECTROPHILES;
D O I
10.1021/ja1017046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new family of organometallic compounds, organozirconium reagents, are shown to serve as suitable partners in cross-coupling reactions of (activated) secondary alkyl electrophiles. Thus, the first catalytic method for coupling secondary alpha-bromoketones with alkenylmetal reagents has been developed, specifically, a mild, versatile, and stereoconvergent carbon-carbon bond-forming process that generates potentially labile beta,gamma-unsaturated ketones with good enantioselectivity.
引用
收藏
页码:5010 / +
页数:3
相关论文
共 15 条
[1]   Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling [J].
Czaplik, Waldemar Maximilian ;
Mayer, Matthias ;
Jacobi von Wangelin, Axel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :607-610
[2]   Catalytic asymmetric Hiyama cross-couplings of racemic α-bromo esters [J].
Dai, Xing ;
Strotman, Neil A. ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3302-+
[3]   Palladium- (and nickel-) catalyzed vinylation of aryl halides [J].
Denmark, Scott E. ;
Butler, Christopher R. .
CHEMICAL COMMUNICATIONS, 2009, (01) :20-33
[4]   Asymmetric Cross-Coupling of Non-Activated Secondary Alkyl Halides [J].
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8347-8349
[5]   Iron-catalyzed cross-coupling of alkyl halides with alkenyl grignard reagents [J].
Guerinot, Amandine ;
Reymond, Sebastien ;
Cossy, Janine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6521-6524
[6]   Enantioselective organo-SOMO catalysis:: The α-vinylation of aldehydes [J].
Kim, Hahn ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :398-+
[7]   Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones [J].
Lou, Sha ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1264-+
[8]   Catalytic Asymmetric Cross-Couplings of Racemic α-Bromoketones with Arylzinc Reagents [J].
Lundin, Pamela M. ;
Esquivias, Jorge ;
Fu, Gregory C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :154-156
[9]  
Negishi E.-i., 2004, Metal-Catalyzed Cross-Coupling Reactions, V2, P815
[10]   Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents [J].
Powell, DA ;
Maki, T ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) :510-511