Highly enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

被引:82
作者
Li, Xuefeng [1 ,2 ,4 ]
Cun, Lingfeng [1 ,2 ]
Lian, Chunxia [1 ,2 ]
Zhong, Ling [1 ,2 ]
Chen, Yingchun [3 ]
Liao, Jian [1 ,2 ]
Zhu, Jin [1 ,2 ]
Deng, Jingen [1 ,2 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmet Synth & Chirotechnol Sichuan Prov, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China
[3] Sichuan Univ, W China Sch Pharm, Chengdu 610041, Peoples R China
[4] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
关键词
D O I
10.1039/b713129a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The highly enantioselective Michael addition of malononitrile to acyclic and cyclic alpha,beta-unsaturated ketones has been developed. The Michael reaction catalyzed by a primary amine derived from quinidine proceeded smoothly and provided the desired adducts with excellent enantioselectivities (83-97% ee).
引用
收藏
页码:349 / 353
页数:5
相关论文
共 47 条
[1]  
Armarego W.L.F., 1997, PURIFICATION LAB CHE
[2]   Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Pesciaioli, Fabio ;
Sambri, Letizia ;
Melchiorre, Paolo .
ORGANIC LETTERS, 2007, 9 (07) :1403-1405
[3]  
BERKESSEL A, 2005, ASYMMETRIC ORGANOCAT, pCH4
[4]   Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols [J].
Black, PJ ;
Edwards, MG ;
Williams, JMJ .
TETRAHEDRON, 2005, 61 (05) :1363-1374
[5]   ENANTIOSELECTIVE CATALYSIS .98. PREPARATION OF 9-AMINO(9-DEOXY)CINCHONA ALKALOIDS [J].
BRUNNER, H ;
BUGLER, J ;
NUBER, B .
TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1699-1702
[6]   Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].
Chen, Wei ;
Du, Wei ;
Duan, Yong-Zheng ;
Wu, Yong ;
Yang, Sheng-Yong ;
Chen, Ying-Chun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670
[7]   Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones [J].
Chen, Wei ;
Du, Wei ;
Yue, Lei ;
Li, Rui ;
Wu, Yong ;
Ding, Li-Sheng ;
Chen, Ying-Chun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) :816-821
[8]   Efficient asymmetric transfer hydrogenation of activated olefins catalyzed by ruthenium amido complexes [J].
Chen, YC ;
Xue, D ;
Deng, JG ;
Cui, X ;
Zhu, J ;
Jiang, YZ .
TETRAHEDRON LETTERS, 2004, 45 (07) :1555-1558
[9]   Recent advances in metal-catalyzed asymmetric conjugate additions [J].
Christoffers, Jens ;
Koripelly, Girish ;
Rosiak, Anna ;
Roessle, Michael .
SYNTHESIS-STUTTGART, 2007, (09) :1279-1300
[10]   Enantioselective Michael addition of nitromethane to α,β-enones catalyzed by chiral quaternary ammonium salts.: A simple synthesis of (R)-baclofen [J].
Corey, EJ ;
Zhang, FY .
ORGANIC LETTERS, 2000, 2 (26) :4257-4259