61235-16-3Relevant academic research and scientific papers
Insights into the role of zirconium in proline functionalized metal-organic frameworks attaining high enantio- and diastereoselectivity
Nguyen, Khoa D.,Kutzscher, Christel,Ehrling, Sebastian,Senkovska,Bon, Volodymyr,de Oliveira, Marcos,Gutmann, Torsten,Buntkowsky, Gerd,Kaskel, Stefan
, p. 41 - 50 (2019)
A chiral zirconium-based catalyst, DUT-67-Pro containing 8-connected Zr6-clusters is obtained by post synthetic functionalization of Zr6O6(OH)2(TDC)4(HCOO)2 (DUT-67, TDC = 2,5-thiophenedicarboxylate) with the chiral monocarboxylic acid, L-proline. 13C and 15N solid state MAS and DNP NMR studies of DUT-67-Pro confirm the integration of L-proline into the porous framework. The chiral MOF catalyst exhibits an excellent catalytic activity at low temperature (298 K) with an unprecedented syn-(S,S)-product selectivity in an asymmetric aldol addition reaction of cyclohexanone to 4-nitrobenzaldehyde (yield = 95%, ee = 96%). Comparative catalytic studies using a molecular Zr6-cluster model compound indicate the Zr6-moiety to be responsible for this inverse diastereoselectivity compared to well-established L-proline organocatalysis and a mechanism is proposed to explain the Zr6-cluster-mediated syn-selectivity. Masking residual acidic active sites in the cluster of the framework was found to be a key prerequisite to achieve the high enantioselectivity. The purely heterogeneous catalytic system based on DUT-67-Pro is highly stable and can be recycled several times.
Reversible regulation of a benzamidine-catalyzed aldol reaction by CO 2
Ilgen, Florian,Konig, Burkhard
, p. 1053 - 1056 (2009)
The catalytic activity of benzamidine during an aldol reaction was reversibly switched on and off with CO2 as an orthogonal signal without affecting the converted substrate or products.
Study of the effect of polymorphism on the self-assembly and catalytic performance of an l-proline based molecular hydrogelator
Díaz-Oltra, Santiago,Berdugo, Cristina,Miravet, Juan F.,Escuder, Beatriu
, p. 3785 - 3791 (2015)
An exhaustive study of the polymorphism found for aggregates and hydrogels of an l-proline based hydrogelator under different preparation conditions is undertaken. The effect of heating temperature, aging time, ultrasound and pH switching on the self-assembly in water has been studied. WAXD analysis of the freeze-dried materials revealed the presence of four polymorphs, three of which could be isolated under specific conditions. Polymorphic differences have been studied by DSC, FTIR, circular dichroism and electron microscopy. Furthermore, the catalytic activity of each polymorph has been tested for the direct aldol reaction between cyclohexanone and 4-nitrobenzaldehyde revealing differences in the reaction rates that could be attributed to differences in molecular packing and aggregate morphology among them. The current study highlights the role that polymorphism plays in the application of functional supramolecular soft materials.
One-pot synthesis of spirooxazino derivatives via enzyme- Initiated multicomponent reactions
Wang, Jun-Liang,Chen, Xiao-Yang,Wu, Qi,Lin, Xian-Fu
, p. 999 - 1005 (2014)
A novel enzyme-initiated multicomponent reaction from readily available aldehyde, nitrostyrene, cyclohexanone and acetamide substrates was discovered, enabling the facile construction of six new C-C/-N bonds and two rings in single step, one-pot operation, for the synthesis of spirooxazino derivatives in moderate to high yields. Several methods such as isotope labelling and enzyme mutation were used to probe the possible mechanism of this complex synthesis.
Asymmetric aldol reaction catalyzed by the self-Assembled nanostructures of L-Proline containing amphiphilic dipeptide: A morphological dependence
Shao, Mingzhe,Jin, Qingxian,Zhang, Li,Liu, Minghua
, p. 1349 - 1350,2 (2012)
An L-proline containing amphiphilic dipeptide was found to self-assemble into nanosphere and nanofiber structures. These nanostructures could catalyze an asymmetric aldol reaction in water. Good reactivity and enantiomeric selectivity was observed for the
Development of fructose-1,6-bisphosphate aldolase enzyme peptide mimics as biocatalysts in direct asymmetric aldol reactions
Brady, Dean,Juma, Wanyama,Makatini, Maya,Peme, Thabo
, p. 36670 - 36681 (2021/12/02)
This study describes the design and synthesis of mimetic peptides modelled on the catalytic active site of the fructose-1,6-bisphosphate aldolase (FBPA) enzyme. The synthesized peptides consisting of the turn motifs and catalytic site amino acids of FBPA
Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions
Anaya de Parrodi, Cecilia,Domínguez-Huerta, Alejandra,Hernández Pérez, Julio M.,Huelgas, Gabriela,Rojas Cabrera, Haydee,Sabala, Rocío,Somanathan, Ratnasamy,de la Higuera Macías, Maximiliano
supporting information, p. 22 - 36 (2020/12/04)
In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1–4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S
Proline-Histidine Dipeptide: A Suitable Template for Generating Ion-Tagged Organocatalysts for the Asymmetric Aldol Reaction
Inani, Heena,Singh, Avtar,Bhati, Meeta,Kumari, Kiran,Kucherenko, Alexander S.,Zlotin, Sergei G.,Easwar, Srinivasan
, p. 2702 - 2712 (2021/06/02)
Proline-histidine dipeptide laid the foundation for the construction of three new ion-tagged organocatalysts, utilising the imidazole moiety of histidine for generating the quaternary species. A brief comparative investigation of the catalysts in the enam
Pro-phe derivatives as organocatalysts in asymmetric aldol reaction
Aydogan, Feray,Karaoglu, Merve,Yolacan, Cigdem
supporting information, p. 233 - 239 (2021/03/19)
The aldol reaction which is the most important one among the C-C bond forming reactions, is widely used by synthetic organic chemists to obtain β-hydroxycarbonyl compounds which are important starting components for biologically active compounds in optica
A chemo-enzymatic oxidation/aldol sequential process directly converts arylbenzyl alcohols and cyclohexanol into chiral β-hydroxy carbonyls
Cheng, Qipeng,Li, Hongyu,Liu, Guohua,Su, Yu,Tan, Chunxia,Wang, Chengyi,Wang, Yu,Xiao, Rui
, p. 7773 - 7779 (2021/10/12)
The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation has great significance, in that it is not only environmentally friendly but also overcomes only a single methodological drawback, either in the chemical or biological process. Herein, through the utilization of the bulky steric hindrance of chiral proline derivatives, an integrated laccase and proline as a chemo-enzymatic co-catalyst system is developed. It enables an efficient oxidation/aldol enantioselective sequential reaction to be accomplished, overcoming the mutual deactivation issue. As we present in this study, this one-pot organic transformation, an initial laccase-mediated oxidation of arylbenzyl alcohols and cyclohexanol to form aldehydes and cyclohexanone, followed by a subsequent proline derivative-catalyzed aldol condensation of the in situ generated intermediates, provides various 1,2-diastereoisomeric chiral β-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.
