71444-29-6Relevant academic research and scientific papers
A highly asymmetric direct aldol reaction catalyzed by chiral proline amide-thiourea bifunctional catalysts
Li, Yun,Yang, Qing-Chuan,Xu, Xiao-Ying,Zhou, Yong,Bai, Jian-Fei,Wang, Fei-Ying,Wang, Li-Xin
, p. 1312 - 1318 (2011)
A series of chiral proline amide-thiourea bifunctional catalysts derived from l-proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields
Engineering a Zirconium MOF through Tandem "click" Reactions: A General Strategy for Quantitative Loading of Bifunctional Groups on the Pore Surface
Zhang, Yingfan,Gui, Bo,Chen, Rufan,Hu, Guiping,Meng, Yi,Yuan, Daqiang,Zeller, Matthias,Wang, Cheng
, p. 2288 - 2295 (2018)
Metal-organic frameworks (MOFs) assembled from linkers of identical length but with different functional groups have gained increasing interests recently. However, it is very challenging for precise control of the ratios of different functionalities. Here
Consequences of folding a water-soluble polymer around an organocatalyst
Huerta, Elisa,Stals, Patrick J. M.,Meijer,Palmans, Anja R. A.
, p. 2906 - 2910 (2013)
Give'em structure: The presence of structuring elements in polymers that were functionalized with catalytic units resulted in a new class of enzyme mimics, which are only active in the folded state (see picture). The conformationally adaptive hydrophobic
Proline Functionalized UiO-67 and UiO-68 Type Metal-Organic Frameworks Showing Reversed Diastereoselectivity in Aldol Addition Reactions
Kutzscher, Christel,Nickerl, Georg,Senkovska, Irena,Bon, Volodymyr,Kaskel, Stefan
, p. 2573 - 2580 (2016)
Functionalization of dicarboxylate linkers with proline was used to generate catalytically active metal-organic frameworks (MOFs) for diastereoselective aldol addition. Due to high robustness and chemical stability, zirconium based MOFs, namely UiO-67 and
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.
Isothiouronium salt based chiral proline amide as efficient bifunctional organocatalyst for direct asymmetric aldol reactions in aqueous medium
Kang, Sungmin,Kim, Taek Hyeon,Yeo, Hyoung Min
supporting information, (2021/08/25)
We developed the first chiral proline amide-isothiouronium based bifunctional organocatalyst, it was prepared by methylation of the corresponding thiourea. This asymmetric catalyst provides aldol products in high to quantitative yields while achieving exc
Biomass waste-derived recyclable heterogeneous catalyst for aqueous aldol reaction and depolymerization of PET waste
Khiangte, Vanlalngaihawma,Laldinpuii, Z. T.,Lalhmangaihzuala, Samson,Lalmuanpuia, Chhakchhuak,Pachuau, Zodinpuia,Vanlaldinpuia, Khiangte
, p. 19542 - 19552 (2021/11/09)
In this work, we discuss the valorization of biomass waste-derived orange peel ash (OPA) by exploring its applicability as a heterogeneous catalyst in aqueous aldol reactions and demonstrating its versatility by promoting the methanolysis of poly(ethylene terephthalate) (PET) waste. The catalyst was characterized using Fourier-transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET) analysis, X-ray powder diffraction (XRD), X-ray fluorescence (XRF), energy dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and thermal gravimetric analysis (TGA) to decode its chemical composition. The aldol reactions were carried out at ambient temperature in the presence of water as a solvent. PET depolymerization was performed in an autoclave for 1 h using only 6% w/w OPA. The catalyst was recovered and reused in both the reactions for up to four successive cycles with minimal loss in the catalytic activity. The use of OPA as a cost-free, eco-friendly and effective recyclable catalyst enables a greener route for C-C bond formation and PET waste recycling.
Application of polyamines and amino acid derivatives based on 2-azabicycloalkane backbone in enantioselective aldol reaction
Iwan, Dominika,Kamińska, Karolina,Wojaczyńska, El?bieta
, (2021/09/04)
Carbon–carbon bond forming reactions, such as aldol reaction and condensation, belong to extremely desired transformations as manifested by >25,000 entries in SciFinder. Their stereoselective variant requires the use of an appropriate catalyst with a stri
Harnessing Additional Capability from in Water Reaction Conditions: Aldol versus Knoevenagel Chemoselectivity
Ali El Damrany Hussein, Hussein,Debnath, Samarpita,Goswami, Falguni,Hussain, Ishtiaq,Karn, Alka,Nakka, Srinuvasu,Nugent, Thomas C.
supporting information, p. 3539 - 3545 (2021/06/12)
Aldol reaction chemoselectivity, racemic or enantioselective, has not been previously demonstrated in the presence of Knoevenagel active functional groups. Here, we show that unhindered β-diketones remain unreacted while a ketone moiety undergoes a highly
A pH-Switchable Aqueous Organocatalysis with Amphiphilic Secondary Amine–Porphyrin Hybrids
Arlegui, Aitor,Crusats, Joaquim,Cuesta, Victor,Moyano, Albert,Torres, Pol
, (2020/07/08)
A series of amphiphilic 5-(cyclic-secondary-amine)-10,15,20-tris(4-sulfonatophenyl)porphyrins, designed with the aim of using the amphiphilic porphyrin moiety for the modulation of the aggregation state of the compound by the pH of the medium, have been synthesised, and the relationship between their supramolecular behaviour in acidic aqueous media and their organocatalytic activity in Michael and aldol reactions has been investigated. In particular, we have found that the catalytic activity of the pyrrolidine moiety in an amphiphilic isoindoline–porphyrin hybrid for the aldol reaction of cyclohexanone with 4-nitrobenzaldehyde can be selectively and reversibly switched on and off by adjusting the homogeneity of its solutions through pH variations. The catalysis of the aldol reaction by the secondary amine moiety would otherwise take place regardless of the pH of the medium. We have demonstrated that the aggregation behaviour of these amine–porphyrin hybrids can be also used for the recovery and reutilization of the catalysts.
