71444-30-9Relevant academic research and scientific papers
Enantioenrichment by Iterative Retro-Aldol/Aldol reaction catalyzed by an achiral or racemic base
Flock, Angelika M.,Reucher, Christine M. M.,Bolm, Carsten
, p. 3918 - 3921 (2010)
Chemical Equation Presented Did nature use the same strategy? The combination of crystal growth and iterative retro-aldol/aldol reactions catalyzed by a simple achiral (or racemic) base allows improvement of the enantiomer ratio of a product obtained from a stereochemically imperfect aldol reaction (see scheme).
An investigation of chiral diamides as organocatalysts in asymmetric aldol reaction
Aydogan, Feray,Yilmaz, Dilek Gul,Yolacan, Cigdem
, (2022/03/08)
Seven novel proline and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (THIQA) based diamides were synthesized successfully by simple amidation reactions and characterized by their spectral data. Their catalytic activities in asymmetric aldol reaction w
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
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
Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis
Arlegui, Aitor,Torres, Pol,Cuesta, Victor,Crusats, Joaquim,Moyano, Albert
, (2020/09/16)
Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, a
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
