Hydroxy-L-prolines as asymmetric catalysts for aldol, Michael addition and Mannich reactions

被引：19
|
作者：
Al-Momani, Lo'ay A. [1 ]
机构：
[1] Tafila Tech Univ, Dept Chem, POB 179, Tafila 66110, Jordan
来源：
ARKIVOC | 2012年
关键词：
Hydroxyprolines; organocatalysis; chemoenzymatic synthesis; amino acids; PROTONIC ACID CATALYSTS; AMINO-ACID; INCREASED REACTIVITY; KETONES; ORGANOCATALYST; MOLECULE; DESIGN;
D O I：
10.3998/ark.5550190.0013.609
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The hydroxyprolines (Hyps) 2-6 are tested as organocatalysts for aldol, Michael additions, and Mannich reactions. The results are compared with the well-known analogous L- proline (1). The effect of the additional hydroxyl group and chiral center was investigated in the three types of reactions. Catalyst 2 shows an enhancement in the stereoselectivity of the aldol reaction, while 3 in Michael addition and 5 in Mannich reaction give the best results. Derivatives of hydroxyprolines show diversity in the catalytic behavior like 6.
引用
收藏
页码：101 / 111
页数：11
相关论文
共 50 条
  • [21] Stereoselective preparation of 3, 5-disubstituted pyrrolidine-3-carboxylic acids as catalysts in asymmetric Aldol and Mannich reactions
    Kotapati, Harikiran
    Robinson, Jamarii
    Masterson, Douglas
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [22] Efficient synthesis of supported proline catalysts for asymmetric aldol reactions
    Elmekawy, A. A.
    Sweeney, J. B.
    Brown, D. R.
    CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (02) : 690 - 696
  • [23] Prolinamides Bearing Thiourea Groups as Catalysts for Asymmetric Aldol Reactions
    Fotaras, Stamatis
    Kokotos, Christoforos G.
    Tsandi, Evaggelia
    Kokotos, George
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (07) : 1310 - 1317
  • [24] L-alaninylated betti bases as catalysts for the asymmetric Michael addition reaction of cyclohexanone to nitroolefins
    Chong-Jun Jiao
    Zong-Xuan Shen
    Guo-Feng Wu
    Jin-Long Zhu
    Ya-Wen Wu
    ACTA CHIMICA SINICA, 2007, 65 (16) : 1631 - 1637
  • [25] Stereoselective sulfonate aldol reactions:: Asymmetric synthesis of α,β-substituted β-hydroxy sulfonates
    Harnying, Wacharee
    Kitisriworaphan, Wipaporn
    Pohmakotr, Manat
    Enders, Dieter
    SYNLETT, 2007, (16) : 2529 - 2532
  • [26] Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions
    Okuyama, Yuko
    Nakano, Hiroto
    Watanabe, Yuki
    Makabe, Mika
    Takeshita, Mitsuhiro
    Uwai, Koji
    Kabuto, Chizuko
    Kwon, Eunsang
    TETRAHEDRON LETTERS, 2009, 50 (02) : 193 - 197
  • [27] Catalytic asymmetric C-H activation as a surrogate of the Aldol and Mannich reactions.
    Davies, HML
    Venkateramani, C
    Antoulinakis, EG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B198 - B198
  • [28] Highly Enantioselective Asymmetric Michael Addition Reactions with New Chiral Multisite Phase-Transfer Catalysts
    Jayaraman, Sivamani
    Kumaraguru, Duraimurugan
    Arockiam, Jesin Beneto
    Paulpandian, Subha
    Rajendiran, Balasaravanan
    Siva, Ayyanar
    SYNLETT, 2014, 25 (12) : 1685 - 1691
  • [29] Chiral pyrrolidine-triazole conjugate catalyst for asymmetric Michael and Aldol reactions
    Chandrasekhar, S.
    Tiwarl, Bhoopendra
    Parida, Bibhuti B.
    Reddy, Ch. Raji
    TETRAHEDRON-ASYMMETRY, 2008, 19 (04) : 495 - 499
  • [30] Cadmium-proline catalyzed direct asymmetric Michael and Aldol reactions in water
    Thingom, Bhavna
    Moirangthem, Soniya D.
    Laitonjam, Warjeet S.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2013, 52 (07): : 929 - 936
12345