Sugar thiourea catalyzed highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone to β-nitroalkenes

被引：18
作者：
Reddy, B. V. Subba [1 ]
Reddy, S. Madhusudana [1 ]
Swain, Manisha [1 ]
机构：
[1] Indian Inst Chem Technol, Lab Xray Crystallog, Ctr Nucl Magnet Resonance, Hyderabad 500607, Andhra Pradesh, India
来源：
RSC ADVANCES | 2013年 / 3卷 / 03期
关键词：
1,4-NAPHTHOQUINONE DERIVATIVES; ANTIFUNGAL; AGENTS; UREA;
D O I：
10.1039/c2ra22270a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone to beta-nitrostyrenes has been achieved using a novel class of sugar-Cinchona thiourea conjugates. The method offers significant advantages such as low catalyst loading (1 mol%), high enantioselectivity (up to 99% ee), short reaction times and ambient reaction conditions.
引用
收藏
页码：930 / 936
页数：7
相关论文
共 33 条
  • [1] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)
    Ballini, R
    Petrini, M
    [J]. TETRAHEDRON, 2004, 60 (05) : 1017 - 1047
  • [2] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [3] A practical, green, and selective approach toward the synthesis of pharmacologically important quinone-containing heterocyclic systems using alumina-catalyzed Michael addition reaction
    Castellano, Sabrina
    Bertamino, Alessia
    Gomez-Monterrey, Isabel
    Santoriello, Marisabella
    Grieco, Paolo
    Campiglia, Pietro
    Sbardella, Gianluca
    Novellino, Ettore
    [J]. TETRAHEDRON LETTERS, 2008, 49 (04) : 583 - 585
  • [4] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts
    Connon, Stephen J.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (22) : 2499 - 2510
  • [5] Antiviral agents 2. Synthesis of trimeric naphthoquinone analogues of conocurvone and their antiviral evaluation against HIV
    Crosby, Ian T.
    Bourke, David G.
    Jones, Eric D.
    de Bruyn, Paula J.
    Rhodes, David
    Vandegraaff, Nick
    Cox, Susan
    Coates, Jonathan A. V.
    Robertson, Alan D.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (17) : 6442 - 6450
  • [6] USFDA-approved disease-modifying treatments for multiple sclerosis - Review of adverse effect profiles
    Galetta, SL
    Markowitz, C
    [J]. CNS DRUGS, 2005, 19 (03) : 239 - 252
  • [7] Structure-activity relationships of novel P2-receptor antagonists structurally related to Reactive Blue 2
    Glänzel, M
    Bültmann, R
    Starke, K
    Frahm, AW
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (12) : 1262 - 1276
  • [8] Constitutional isomers of Reactive Blue 2 -: selective P2Y-receptor antagonists?
    Glänzel, M
    Bültmann, R
    Starke, K
    Frahm, AW
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (03) : 303 - 312
  • [9] Synthesis and cytotoxic evaluation of novel spirohydantoin derivatives of the dihydrothieno[2,3-b]naphtho-4,9-dione system
    Gomez-Monterrey, I
    Santelli, G
    Campiglia, P
    Califano, D
    Falasconi, F
    Pisano, C
    Vesci, L
    Lama, T
    Grieco, P
    Novellino, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) : 1152 - 1157
  • [10] Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates
    Hsin, Ling-Wei
    Wang, Hui-Po
    Kao, Pi-Hung
    Lee, On
    Chen, Wan-Ru
    Chen, Hung-Wei
    Guh, Jih-Hwa
    Chan, Ya-Ling
    His, Chin-Ping
    Yang, Ming-Show
    Li, Tsai-Kun
    Lee, Chieh-Hua
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (02) : 1006 - 1014
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