Highly enantioselective Michael additions of α-cyanoacetate with chalcones catalyzed by bifunctional cinchona-derived thiourea organocatalyst

被引：59
|
作者：
Gu, Chun-ling
Liu, Li [1 ]
Sui, Yong
Zhao, Jun-Lin
Wang, Dong
Chen, Yong-Jun
机构：
[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 04期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/j.tetasy.2007.02.016
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The conjugate addition of ethyl alpha-cyanoacetate with chalcones has been developed. In the presence of cinchona alkaloid-derived thiourea organocatalyst 1i (10 mol %), ethyl alpha-cyanoacetate could react with various chalcones to afford Michael adducts with high yields (80-92%) and enantioselectivities (83-95% ee). (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：455 / 463
页数：9
相关论文
共 50 条
  • [21] Cysteine-derived organocatalyst in a highly enantioselective intramolecular Michael reaction
    Hayashi, Y
    Gotoh, H
    Tamura, T
    Yamaguchi, H
    Masui, R
    Shoji, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16028 - 16029
  • [22] Chiral Bifunctional Thiourea-Catalyzed Enantioselective Michael Addition of Ketones to Nitrodienes
    Ma, Hai
    Liu, Kun
    Zhang, Fa-Guang
    Zhu, Chuan-Le
    Nie, Jing
    Ma, Jun-An
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05): : 1402 - 1409
  • [23] Bifunctional cinchona alkaloid-squaramide-catalyzed highly enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones
    Ghosh, Arun K.
    Zhou, Bing
    TETRAHEDRON LETTERS, 2013, 54 (27) : 3500 - 3502
  • [24] Epi-cinchona based thiourea organocatalyst family as an efficient asymmetric Michael addition promoter:: Enantioselective conjugate addition of nitroalkanes to chalcones and α,β-unsaturated N-acylpyrroles
    Vakulya, Benedek
    Varga, Szilard
    Soos, Tibor
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09): : 3475 - 3480
  • [25] Highly enantioselective and practical cinchona-derived phase-transfer catalysts for the synthesis of α-amino acids
    Park, HG
    Jeong, BS
    Yoo, MS
    Lee, JH
    Park, MK
    Lee, YJ
    Kim, MJ
    Jew, SS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (16) : 3036 - 3038
  • [26] Highly enantioselective Michael addition of 2-oxindoles to vinyl selenone in RTILs catalyzed by a Cinchona alkaloid-based thiourea
    Zhang, Tao
    Cheng, Liang
    Hameed, Shahid
    Liu, Li
    Wang, Dong
    Chen, Yong-Jun
    CHEMICAL COMMUNICATIONS, 2011, 47 (23) : 6644 - 6646
  • [27] Interplay of Direct Stereocontrol and Dynamic Kinetic Resolution in a Bifunctional Amine Thiourea Catalyzed Highly Enantioselective Cascade Michael-Michael Reaction
    Yu, Chenguang
    Zhang, Yinan
    Song, Aiguo
    Ji, Yafei
    Wang, Wei
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) : 770 - 774
  • [28] Enantioselective Synthesis of Chromanones via a Tryptophan- Derived Bifunctional Thiourea-Catalyzed Oxa-Michael-Michael Cascade Reaction
    Wang, Haifei
    Luo, Jie
    Han, Xiao
    Lu, Yixin
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 2971 - 2975
  • [29] Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst
    Saha, Prasenjit
    Biswas, Arnab
    Molleti, Nagaraju
    Singh, Vinod K.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21): : 11115 - 11122
  • [30] Enantioselective tandem Michael reaction to nitroalkene catalyzed by bifunctional thiourea: total synthesis of (-)-epibatidine
    Hoashi, Y
    Yabuta, T
    Yuan, P
    Miyabe, H
    Takemoto, Y
    TETRAHEDRON, 2006, 62 (2-3) : 365 - 374
12345