Applications of biological urea-based catalysts in chemical processes

被引:57
作者
Atashkar, Bahareh [1 ]
Zolfigol, Mohammad Ali [1 ]
Mallakpour, Shadpour [2 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Deportment Organ Chem, Hamadan 6517838683, Iran
[2] Isfahan Univ Technol, Dept Chem, Esfahan 8415683111, Iran
基金
美国国家科学基金会;
关键词
Urea; Catalyst; Hydrogen-bonding catalyst; Chiral urea; Enantioselective reactions; BAYLIS-HILLMAN REACTION; N-SULFINYL UREA; ASYMMETRIC ALPHA-HYDROXYLATION; MOLECULAR-DYNAMICS SIMULATIONS; DIELS-ALDER REACTIONS; SILICA SULFURIC-ACID; ONE-POT SYNTHESIS; BIFUNCTIONAL ORGANOCATALYST; ENANTIOSELECTIVE SYNTHESIS; GUANIDINIUM CHLORIDE;
D O I
10.1016/j.mcat.2018.03.009
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
The present critical review outlines the close relationship and mutual interplay between molecular recognition, active site considerations in enzyme catalysis involving organocatalysis via hydrogen bonding. These interconnections are generally not made although; as we demonstrated they are quite apparent as exemplified with pertinent examples in the field of urea organocatalysis. Urea organocatalysis derivatives have been used as efficient Lewis-acidic catalysts due to effective H-bonding, basic catalyst, coupling with metals as catalyst, chiral acid catalysts, urea anions catalysts, coupling with ionic liquids, urea polymer catalysts and immobilization on solid acid and magnetic nanoparticle supports. Consecutively, the discovery and mechanistic elucidation of such reactions are likely to improve the understanding of enzyme active sites.
引用
收藏
页码:192 / 246
页数:55
相关论文
共 250 条
[51]   Palladium nanoclusters supported on propylurea-modified siliceous mesocellular foam for coupling and hydrogenation reactions [J].
Erathodiyil, Nandanan ;
Ooi, Samuel ;
Seayad, Abdul M. ;
Han, Yu ;
Lee, Su Seong ;
Ying, Jackie Y. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (10) :3118-3125
[52]   HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS [J].
ETTER, MC ;
URBANCZYKLIPKOWSKA, Z ;
ZIAEBRAHIMI, M ;
PANUNTO, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8415-8426
[53]   NUCLEAR MAGNETIC-RESONANCE STUDIES OF AQUEOUS UREA SOLUTIONS [J].
FINER, EG ;
FRANKS, F ;
TAIT, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (13) :4424-&
[54]   Computational study-led organocatalyst design: A novel, highly active urea-based catalyst for addition reactions to epoxides [J].
Fleming, Eimear M. ;
Quigley, Cormac ;
Rozas, Isabel ;
Connon, Stephen J. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03) :948-956
[55]   Novel axially chiral bis-arylthiourea-based organocatalysts for asymmetric Friedel-Crafts type reactions [J].
Fleming, Eimear M. ;
McCabe, Thomas ;
Connon, Stephen J. .
TETRAHEDRON LETTERS, 2006, 47 (39) :7037-7042
[56]   Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters [J].
Fortner, Kevin C. ;
Shair, Matthew D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1032-1033
[57]   STRUCTURAL APPROACH TO SOLVENT POWER OF WATER FOR HYDROCARBONS - UREA AS A STRUCTURE BREAKER [J].
FRANK, HS ;
FRANKS, F .
JOURNAL OF CHEMICAL PHYSICS, 1968, 48 (10) :4746-&
[58]   H-bonding organocatalysed Friedel-Crafts alkylation of aromatic and heteroaromatic systems with nitroolefins [J].
Gabriella, D ;
Herrera, RP ;
Riccia, A .
SYNLETT, 2004, (13) :2374-2378
[59]   Bifunctional (Thio)urea-Phosphine Organocatalysts Derived from d-Glucose and -Amino Acids and Their Application to the Enantioselective Morita-Baylis-Hillman Reaction [J].
Gergelitsova, I. ;
Tauchman, J. ;
Cisarova, I. ;
Vesely, J. .
SYNLETT, 2015, 26 (19) :2690-2696
[60]   Magnetic nanoparticles supported oxime palladacycle as a highly efficient and separable catalyst for room temperature Suzuki-Miyaura coupling reaction in aqueous media [J].
Gholinejad, Mohammad ;
Razeghi, Mehran ;
Najera, Carmen .
RSC ADVANCES, 2015, 5 (61) :49568-49576