174173-19-4Relevant articles and documents
Design of New Amino Tf-Amide Organocatalysts: Environmentally Benign Approach to Asymmetric Aldol Synthesis
Lee, Hyo-Jun,Arumugam, Natarajan,Almansour, Abdulrahman I.,Kumar, Raju Suresh,Maruoka, Keiji
, p. 401 - 404 (2019)
A new type of optically pure primary amino aromatic Tf-amide organocatalyst can be easily prepared from 8-amino-1-tetralone, and its chemical behavior was investigated in the context of asymmetric aldol and Mannich reactions. Most notably, the asymmetric
The Chemistry of Chlorosilyl Enolates 3.: Variation of the Silyl Group and the Effect on Rate and Enantiomeric Excess of Acetate Aldol Additions
Denmark, Scott E.,Winter, Stephen B. D.
, p. 1087 - 1089 (1997)
The rales of reaction of the silyl ketene acetals CH2=C(OMe)OSiCl2R (1a-d) with benzaldehyde and pivalaldehyde have been determined and follow the order R = H ～ Cl > Ph > Me. These reactions are promoted by catalytic amounts of a chiral phosphoramide; enantioselectivities of the products obtained show a high sensitivity towards variation of the silyl group. The reactions of the dialkyl substituted chlorosilyl enolates CH2=C(OMe)OSiClR2 (1e,f) with benzaldehyde are not promoted by HMPA.
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
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
Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction
Martins, Rafaela de S.,Pereira, Mathias P.,de Castro, Pedro P.,Bombonato, Fernanda I.
, (2019/12/24)
The preparation of four novel organocatalysts as highly diastereo and enantioselective catalysts for the solvent-free asymmetric aldol reaction was described. These organocatalysts were synthesized in eight steps applying simple and commercially available starting materials. The best results were obtained for the proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.
Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions
Kooti,Kooshki,Nasiri
, p. 2641 - 2656 (2019/02/14)
A new catalyst has been prepared via immobilization of Cu(proline)2 complex onto the surface of magnetic graphene. The fabricated nanocatalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD) analysis, vibrating-sample magnetometry (VSM), scanning electron microscopy (SEM), energy-dispersive X-ray (EDX) spectroscopy, transmission electron microscopy (TEM), inductively coupled plasma (ICP) techniques, and elemental analysis. Its catalytic performance was investigated in the aldol reaction using a mild and ecofriendly procedure. The synthesized nanocomposite, which contains Cu(II) center as Lewis acid, was found to be an efficient catalyst for asymmetric aldol reactions, affording corresponding aldol products in high yield and excellent enantiomeric excess (> 90?%). The examined catalyst was prepared from low-cost, easily available starting materials and can be readily isolated by magnetic decantation for recycling and reuse in consecutive reactions without significant loss of activity.
Evaluation of Amino Nitriles and an Amino Imidate as Organo?-catalysts in Aldol Reactions
Brown, Alexander J.,Clarke, Paul A.,Vagkidis, Nikolaos
supporting information, p. 4106 - 4112 (2019/10/28)
The efficiency of l -valine and l -proline nitriles and a tert -butyl?- l -proline imidate as organocatalysts for the aldol reaction have been evaluated. l -Valine nitrile was found to be a syn -selective catalyst, while l -proline nitrile was found to be anti -selective, and gave products in modest to good enantioselectivities. tert -Butyl l -proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti -selectivity. The enantioselectivity of the tert -butyl l -proline imidate was found to be good to excellent, with products being formed in up to 94percent enantiomeric excess.
