Organocatalytic asymmetric vinylogous addition to quinones -: formation of optically active α-aryl ketones

被引:69
作者
Aleman, Jose [1 ]
Jacobsen, Christian Borch [1 ]
Frisch, Kim [1 ]
Overgaard, Jacob [1 ]
Jorgensen, Karl Anker [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus, Denmark
关键词
D O I
10.1039/b716485h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first organocatalytic addition of dicyanoalkylidenes to quinones catalyzed by Cinchona alkaloids leading to formation of 1,4-diketone derivatives with high diastereomeric ratios ( up to >98 : <2 dr) and enantioselectivities ( up to 99% ee) has been developed; the optically active compounds obtained are useful for a number of transformations, e. g. the synthesis of optically active alpha-aryl ketones.
引用
收藏
页码:632 / 634
页数:3
相关论文
共 28 条
[1]   Asymmetric organocatalytic α-arylation of aldehydes [J].
Aleman, Jose ;
Cabrera, Silvia ;
Maerten, Eddy ;
Overgaard, Jacob ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5520-5523
[2]   Organocatalytic asymmetric "anti-Michael" reaction of β-ketoesters [J].
Aleman, Jose ;
Reyes, Efraim ;
Richter, Bo ;
Overgaard, Jacob ;
Jorgensen, Karl Anker .
CHEMICAL COMMUNICATIONS, 2007, (38) :3921-3923
[3]   Organocatalytic highly enantioselective α-arylation of β-ketoesters [J].
Aleman, Jose ;
Richter, Bo ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5515-5519
[4]  
[Anonymous], ACC CHEM RES
[5]   Organocatalytic asymmetric deconjugative Michael additions [J].
Bell, Mark ;
Frisch, Kim ;
Anker Jorgensen, Karl .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5407-5410
[6]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[7]   An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers [J].
Bogle, Katherine M. ;
Hirst, David J. ;
Dixon, Darren J. .
ORGANIC LETTERS, 2007, 9 (23) :4901-4904
[8]  
Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[9]  
Dalko P.I., 2007, ENANTIOSELECTIVE ORG
[10]  
Dalko P. I., 2001, ANGEW CHEM-GER EDIT, V113, P3840