Organocatalytic Asymmetric Michael Addition of Ketones toα,β-Unsaturated Nitro Compounds

被引：11
|
作者：
Shim, Jae Ho [1 ]
Nam, Si Hun [1 ]
Kim, Byeong-Seon [2 ,3 ]
Ha, Deok-Chan [1 ]
机构：
[1] Korea Univ, Res Inst Nat Sci, Dept Chem, 145 Anam Ro, Seoul 02841, South Korea
[2] Gyeongsang Natl Univ, Dept Chem Educ, Jinju 52828, South Korea
[3] Gyeongsang Natl Univ, Res Inst Nat Sci, Jinju 52828, South Korea
来源：
CATALYSTS | 2020年 / 10卷 / 06期
基金：
新加坡国家研究基金会;
关键词：
organocatalyst; enantioselectivity; yield; thiourea catalyst; asymmetric; CONJUGATE ADDITION; AROMATIC KETONES; CATALYSTS; ENANTIOMERS; AMINES; DONORS;
D O I：
10.3390/catal10060618
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
An organic catalyst "(R,R)-1,2-diphenylethylenediamine(DPEN) derivative'' was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones totrans-beta-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition provides high chemical yield and enantioselectivities (ee) (up to 96% yield, 98% ee).
引用
收藏
页数：11
相关论文
共 50 条
  • [21] Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones
    Dalpozzo, Renato
    Bartoli, Giuseppe
    Bencivenni, Giorgio
    SYMMETRY-BASEL, 2011, 3 (01): : 84 - 125
  • [22] Michael Addition of Thiols to á, -Unsaturated Carbonyl Compounds Catalyzed by Bifunctional Organocatalysts: Asymmetric Michael Addition and Asymmetric Protonation
    LI BangJing JIANG Lin LIU Min DING LiSheng CHEN YingChun West China School of Pharmacy Sichuan University Chengdu China Chengdu Institute of Biology Chinese Academy of Sciences Chengdu China
    合成化学, 2004, (S1) : 48 - 48
  • [23] Chiral Thiophosphoramidate-Catalyzed Asymmetric Michael Addition of Ketones to Nitro Olefins
    Lu, Aidang
    Wu, Ronghua
    Wang, Youming
    Zhou, Zhenghong
    Wu, Guiping
    Fang, Jianxin
    Tang, Chuchi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (11) : 2057 - 2061
  • [24] Organocatalytic asymmetric Michael-type reaction between β,γ-unsaturated α-keto ester and α-nitro ketone
    Li, Pengfei
    Chan, Sau Hing
    Chan, Albert S. C.
    Kwong, Fuk Yee
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (23) : 7997 - 7999
  • [25] A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations
    Emori, E
    Arai, T
    Sasai, H
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) : 4043 - 4044
  • [26] Organocatalytic Michael addition-lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents
    Morrill, Louis C.
    Stark, Daniel G.
    Taylor, James E.
    Smith, Siobhan R.
    Squires, James A.
    D'Hollander, Agathe C. A.
    Simal, Carmen
    Shapland, Peter
    O'Riordan, Timothy J. C.
    Smith, Andrew D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (44) : 9016 - 9027
  • [27] Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to β,γ-Unsaturated α-Keto Esters
    Lee, Hyun Joo
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (11): : 3537 - 3538
  • [28] Asymmetric Organocatalytic Michael Addition of α,β-Unsaturated Ketone with 1,2,4-Triazole
    Zhou, Yufeng
    Li, Xin
    Li, Wenjun
    Wu, Chunlin
    Liang, Xinmiao
    Ye, Jinxing
    SYNLETT, 2010, (15) : 2357 - 2360
  • [29] Organocatalytic Enantioselective Michael Addition of 4-Hydroxycoumarin to α,β-Unsaturated Ketones: A Simple Synthesis of Warfarin
    Dong, Zhenhua
    Wang, Lijia
    Chen, Xiaohong
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (30) : 5192 - 5197
  • [30] Organocatalytic asymmetric Michael addition of pyrazoleamides to β-phthalimidonitroethene
    Luo, Yuan
    Xie, Ke-Xin
    Yue, Deng-Feng
    Zhang, Xiao-Mei
    Xu, Xiao-Ying
    Yuan, Wei-Cheng
    TETRAHEDRON, 2017, 73 (43) : 6217 - 6222
12345