Back to Natural Cinchona Alkaloids: Highly Enantioselective Michael Addition of Malononitrile to Enones

被引：64
|
作者：
Russo, Alessio [1 ]
Perfetto, Alessandra [1 ]
Lattanzi, Alessandra [1 ]
机构：
[1] Univ Salerno, Dipartimento Chim, I-84084 Fisciano, Italy
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 18期
关键词：
Cinchona alkaloids; enones; malononitrile; Michael addition; organocatalysis; ASYMMETRIC CONJUGATE ADDITION; SUBSTITUTED ALPHA-CYANOACETATES; 1,3-DICARBONYL COMPOUNDS; QUATERNARY STEREOCENTERS; ALPHA; BETA-UNSATURATED KETONES; MALONATE ESTERS; CATALYSTS; EFFICIENT; NITROALKANES; CONSTRUCTION;
D O I：
10.1002/adsc.200900712
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy route to difficultly accessible ester derivatives has been also disclosed.
引用
收藏
页码：3067 / 3071
页数：5
相关论文
共 50 条
  • [1] Enantioselective Michael addition catalyzed by cinchona alkaloids
    Szöllösi, G
    Bartók, M
    [J]. CHIRALITY, 2001, 13 (10) : 614 - 618
  • [2] Highly enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
    Li, Xuefeng
    Cun, Lingfeng
    Lian, Chunxia
    Zhong, Ling
    Chen, Yingchun
    Liao, Jian
    Zhu, Jin
    Deng, Jingen
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (02) : 349 - 353
  • [3] Enantioselective Michael Addition of Malonates to Enones
    Bako, Peter
    Nemcsok, Tamas
    Rapi, Zsolt
    Keglevich, Gyorgy
    [J]. CURRENT ORGANIC CHEMISTRY, 2020, 24 (07) : 746 - 773
  • [4] Highly enantioselective Michael addition of malononitrile to α,β-unsaturated pyrazolamides catalyzed by a bifunctional thiourea
    Zheng, Yuanqin
    Yao, Yongqi
    Ye, Ling
    Shi, Zhichuan
    Li, Xuefeng
    Zhao, Zhigang
    Li, Xinying
    [J]. TETRAHEDRON, 2016, 72 (07) : 973 - 978
  • [5] Highly enantioselective conjugate addition of nitroalkanes to enones catalyzed by cinchona alkaloid derived primary amine
    Liu, Wenjing
    Mei, Desheng
    Wang, Wei
    Duan, Wenhu
    [J]. TETRAHEDRON LETTERS, 2013, 54 (29) : 3791 - 3793
  • [6] Enantioselective phenylacetylene addition to aldehydes induced by Cinchona alkaloids
    Kamble, RM
    Singh, VK
    [J]. TETRAHEDRON LETTERS, 2003, 44 (28) : 5347 - 5349
  • [7] Diphenylprolinol methyl ether: A highly enantioselective catalyst for Michael addition of aldehydes to simple enones
    Chi, YG
    Gellman, SH
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4253 - 4256
  • [8] An enantioselective synthesis of natural (-)-huperzine A via cinchona alkaloids-promoted asymmetric Michael reaction
    Kaneko, S
    Yoshino, T
    Katoh, T
    Terashima, S
    [J]. HETEROCYCLES, 1997, 46 : 27 - 30
  • [9] Using Natural Cinchona Alkaloids to Promote the Enantioselective Addition of Dialkylzinc to N-Diphenylphosphinylimines
    张海乐
    方春梅
    李昕
    龚流柱
    宓爱巧
    崔欣
    蒋耀忠
    [J]. Chinese Journal of Chemistry, 2003, (07) : 955 - 959
  • [10] Using natural cinchona alkaloids to promote the enantioselective addition of dialkylzinc to N-diphenylphosphinylimines
    Zhang, HL
    Fang, CM
    Li, X
    Gong, LZ
    Mi, AQ
    Cui, X
    Jiang, YZ
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (07) : 955 - 959
12345