61235-09-4Relevant academic research and scientific papers
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.
“Ship-in-a-Bottle” Strategy for Immobilization of 9-Amino(9-deoxy)epi-Cinchona Alkaloid into Molecularly Imprinted Solid Acid: Acetal Hydrolysis/Asymmetric Aldol Tandem Reaction
Wei, Shuai,Zhang, Jianing,Li, Shan,Ma, Xuebing
, p. 627 - 636 (2020/12/09)
Direct immobilization of versatile 9-amino(9-deoxy)epi-cinchona alkaloids without molecule modification to achieve heterogeneous organocatalysis is of interest in the low-cost production of optically active compounds. In this paper, an exquisite “ship-in-a-bottle” strategy for direct and simple immobilization of 9-amino-(9-deoxy)epi-quinine (QNNH2) into hollow polystyrene nano-bowl with imprinted free space around ?SO3H was developed via acid-base reaction and radical polymerization. The heterogeneous organocatalyst with 0.44 mmol g?1 of QNNH2 and 0.48 mmol g?1 of residual ?SO3H possessed fast mass transfer due to the characteristic architectural features, such as thin shell thickness, free space around catalytic site, and hollow interior. In heterogeneous acetal hydrolysis/asymmetric aldol tandem reaction, good to excellent catalytic performances (90–95 % yields, anti/syn=88/12–96/4, and 97–99 % ee anti) for acetals bearing electron-withdrawing substituents (R=o, m, p-NO2, Cl) were achieved. The “ship-in-a-bottle” QNNH2 displayed good stability and reusability with excellent catalytic performances in the reuses.
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
New small γ-turn type: N -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes
Begum, Zubeda,Kwon, Eunsang,Nakano, Hiroto,Okuyama, Yuko,Seki, Chigusa,Takeshita, Mitsuhiro,Thiyagarajan, Rajkumar,Tokiwa, Michio,Tokiwa, Suguru,Uwai, Koji
, p. 38925 - 38932 (2021/12/20)
New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn?:?anti/13?:?87 dr, up to 99% ee). This journal is
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
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
supporting information, 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.
New Mesoporous silica-supported organocatalysts based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, reusable, and heterogeneous catalysts for the asymmetric aldol reaction
Juaristi, Eusebio,Romero-Sedglach, Kevin A.,Sánchez-Antonio, Omar,Vázquez-Orta, Erika C.
, (2020/10/18)
Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol rea
A Zn(II)-Coordination Polymer for the Instantaneous Cleavage of Csp3-Csp3 Bond and Simultaneous Reduction of Ketone to Alcohol
Das, Gourab Kanti,Dey, Biswajit,Dhibar, Subhendu,Ghosh, Debasish,Gupta, Vivek K.
supporting information, (2020/04/10)
Two coordination polymers of Zn(II) and Cu(II) with n-butylmalonic acid have been achieved in this work. The crystallographic structural descriptions along with the sedimentary rock-type microstructural morphology of these two coordination polymers (CPs) have been explored. The reactivity of β-hydroxy ketones with these two CPs has also been investigated. The Zn(II)-CP shows a specific reactivity with β-hydroxy ketone at room temperature and in open air conditions. Through a microcolumn-based filtration technique, the Zn(II)-CP shows the capability to break the Csp3-Csp3 σ bonds of β-hydroxy ketone and simultaneously reduce the associated ketone to alcohol. Such conversion has been progressed without the use of any additional external reducing agent and any chemical workup or column chromatographic purification protocol. Other similar type CPs of Cu(II) and Mn(II) with n-butylmalonic acid completely failed to show similar reactivity with β-hydroxy ketone. On the basis of much experimental evidence, the most possible mechanistic pathway of the reactivity between β-hydroxy ketone and Zn(II)-CP has also been proposed through this work.
Self-assembled Polydiacetylene Nanoribbons for Semi-heterogeneous and Enantioselective Organocatalysis of Aldol Reactions in Water
Hoang, Minh-Duc,Kumar, Ramar Arun,Buisson, David A.,Ling, Wai Li,Gravel, Edmond,Doris, Eric
, p. 1156 - 1160 (2020/01/02)
We report the synthesis, characterization, and supra-molecular assembly of novel diacetylene amphiphilic units bearing a chiral proline-derived head group. In water, these amphiphiles self-assemble into twisted ribbons that are photo-polymerized to afford
Chiral proline sulfonamide bifunctional catalyst and preparation method and application thereof
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Paragraph 0097-0100, (2020/08/17)
The invention discloses a novel chiral sulfonamide bifunctional catalyst and a preparation method and application thereof. The catalyst comprises a compound A or a compound B. The molecular structureof the compound A is shown as a formula (I) which is des
