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
  • [41] A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions
    Ishii, T
    Fujioka, S
    Sekiguchi, Y
    Kotsuki, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9558 - 9559
  • [42] Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions
    Pandya, Bhaumik A.
    Dandapani, Sivaraman
    Duvall, Jeremy R.
    Rowley, Ann
    Mulrooney, Carol A.
    Ryba, Troy
    Dombrowski, Michael
    Harton, Marie
    Young, Damian W.
    Marcaurelle, Lisa A.
    TETRAHEDRON, 2011, 67 (34) : 6131 - 6137
  • [43] Self-Assembled Supramolecular Gels for Catalyzing Asymmetric Aldol and Mannich Reactions in Aqueous Media
    Huang, Jiahe
    Zhang, Chunhong
    Bai, Jianwei
    Wang, Yudan
    Satoh, Toshifumi
    Lin, Feng-Huei
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2025,
  • [44] Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
    Barros, Maria Teresa
    Phillips, Ana Maria Faisca
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) : 178 - 185
  • [45] NOVEL REACTIVE SILYL ENOLATES - HIGHLY STEREOSELECTIVE ALDOL AND MICHAEL REACTIONS WITHOUT CATALYSTS
    KOBAYASHI, S
    NISHIO, K
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10): : 2647 - 2649
  • [46] 1,5-asymmetric induction in methyl ketone aldol addition reactions
    Evans, DA
    Coleman, PJ
    Cote, B
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04): : 788 - 789
  • [47] Enantioselectivity switch in asymmetric Michael addition reactions using phosphonium salts
    Fang, Guosheng
    Wang, Hongyu
    Zheng, Changwu
    Pan, Lu
    Zhao, Gang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (28) : 6334 - 6340
  • [48] Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β-Unsaturated Nitroolefins
    Das, Tapaswini
    Mohapatra, Seetaram
    Mishra, Nilima P.
    Nayak, Sabita
    Raiguru, Bishnu P.
    CHEMISTRYSELECT, 2021, 6 (15): : 3745 - 3781
  • [49] Enantioselective Michael addition reactions catalyzed by a new heterobimetallic asymmetric complex
    Choudary, BM
    Chowdari, NS
    Kantam, ML
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 142 (03) : 389 - 392
  • [50] The Role of Noninnocent Solvent Molecules in Organocatalyzed Asymmetric Michael Addition Reactions
    Patil, Mahendra P.
    Sunoj, Raghavan B.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (33) : 10472 - 10485
12345