56072-25-4Relevant academic research and scientific papers
Dendritic HMPA as a promoter for the mukaiyama aldol and allylation reaction
Mummy, Florian,Haag, Rainer
, p. 2672 - 2676 (2012)
We synthesized a hexamethylphosphoramide (HMPA) analogue that was immobilized on hyperbranched polyglycerol (hPG) via a covalent approach. This polymeric analogue (hPG-HMPA) can potentially replace carcinogenic HMPA as a Lewis base additive in many reactions involving trichlorosilyl substrates. We investigated immobilized HMPA in the Mukaiyama aldol and allylation reactions. In most cases, yields and selectivities of supported and nonsupported HMPA were similar. Moreover, in the allylation reaction a positive dendritic effect could be observed, and the loading of HMPA could be lowered with hPG-HMPA to catalytic quantities (0.5 mol%). These results demonstrate that the use of HMPA can be avoided by hPG-HMPA without loss in terms of yield or selectivity. Georg Thieme Verlag KG Stuttgart · New York.
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.
Natural eutectogels: Sustainable catalytic systems for C-C bond formation reactions
D'Anna, Francesca,Meli, Alessandro,Ramón, Diego J.,Rizzo, Carla,Saavedra, Beatriz
supporting information, p. 6555 - 6565 (2021/09/10)
Natural eutectogels were prepared by combining the properties of amino acids with the ones of deep eutectic solvents. The soft materials obtained were fully characterised by determining the gel-sol transition temperatures and analysing the mechanical and
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
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
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.
Organocatalytic asymmetric aldol reaction using protonated chiral 1,2-diamines
Shim, Jae Ho,Kim, Min-Joon,Lee, Ji Yeon,Kim, Kyoung Hoon,Ha, Deok-Chan
supporting information, (2020/08/14)
Organic-catalyzed stereoselective reactions have gained attention because they avoid the problems associated with metal catalysts, but existing catalysts based on proline have limitations. Therefore, (R,R)-(+)-1,2-diphenylethylenediamine (DPEN) was select
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
