10029-04-6Relevant academic research and scientific papers
An efficient synthesis of alkyl α-(hydroxymethyl)acrylates induced by DABCO in an aqueous medium
Turki, Taoufik,Villiéras, Jean,Amri, Hassen
, p. 3071 - 3072 (2005)
Alkyl α-(hydroxymethyl)acrylates are prepared in high yields on a synthetic scale by hydroxymethylation of the corresponding acrylates using 30% aqueous formaldehyde in THF or DME as solvent and DABCO as the catalyst.
Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation
Horn, Alexander,Kazmaier, Uli
, p. 4595 - 4599 (2019)
N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.
Iterative Synthesis of Polydeoxypropionates Based on Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted Acrylic Acids
Che, Wen,Wen, Danyang C.,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 3305 - 3309 (2018)
A novel iterative protocol for the synthesis of polydeoxypropionates was developed based on iridium-catalyzed asymmetric hydrogenation of α-substituted acrylic acids. The catalyst loading can be as low as 0.01 mol %, and the overall yield for one iterativ
Convenient general asymmetric synthesis of roche ester derivatives through catalytic asymmetric hydrogenation: Steric and electronic effects of ligands
Pautigny, Cyrielle,Jeulin, Severine,Ayad, Tahar,Zhang, Zhaoguo,Genet, Jean-Pierre,Ratovelomanana-Vidal, Virginie
, p. 2525 - 2532 (2008)
An efficient and concise asymmetric hydrogenation of acrylate esters promoted by the cationic ruthenium monohydride complex [Ru(H) (hη6-cot)SYNPHOS]+BF44- is reported. A full investigation of the effects of catalyst precursors, solvents, temperature, hydrogen pressure, substrates as well as steric and electronic properties of ligands was carried out. The corresponding valuable Roche ester derivatives were obtained in good to excellent isolated yields and high enantioselectivities under mild conditions. The robustness and practicability of this highly enantioselective hydrogenation was demonstrated by the synthesis of the 3-hydroxy-2-methylpropanoic acid tert-butyl ester on a multigram scale, resulting in excellent yield and ee up to 94%.
Total synthesis and absolute configuration of curvularides A-E
Sudhakar, Gangarajula,Satish, Kovela,Raghavaiah, Jakka
, p. 10010 - 10020 (2012)
The first total synthesis of curvularides A-E, isolated from a culture broth of the endophytic fungus Curvularia geniculata, is described. The divergent total synthesis reported herein confirmed the absolute configurations of curvularides A-E and supported that these natural products might be obtained from a common biosynthetic pathway. The key steps involved in the synthesis were the diastereoselective hydrogenation of exo-methylene-γ-butyrolactone to α-methyl-γ-butyrolactone, Sharpless kinetic resolution, Sharpless asymmetric epoxidations, and intramolecular and intermolecular epoxide openings.
Total Synthesis of Clavilactone B: A Radical Cyclization-Fragmentation Strategy
Suizu, Hiroshi,Shigeoka, Daisuke,Aoyama, Hiroshi,Yoshimitsu, Takehiko
, p. 126 - 129 (2014)
A new synthetic route to clavilactone B, a naturally occurring inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase, is disclosed. The route features a sequential samarium-mediated radical cyclization-fragmentation of an indanone derivativ
Effect of Lewis acids and low temperature initiators on the allyl transfer reaction involving phthalimido-N-oxyl radical
Patil, Shradha,Chen, Liang,Tanko, James M.
, p. 7029 - 7033 (2014)
Previously, we reported allyl transfer reactions of allyl bromide and allyl phthalimido-N-oxyl substrates with hydrocarbons that result in CC bond formation. In both cases, efficient chain transfer processes along with high reaction yields were observed. Since PINO chemistry leads to an environmentally friendly method of hydrocarbon functionalization, additional studies were performed in order to improve the process. To expand the utility of this reaction, we carried out experiments to optimize reaction conditions and tested the effect of Lewis acids and low temperature initiators. Although allyl-PINO substrates reacted slightly slower than the bromides, the reactions were cleaner with little or no side products. The chain lengths for these reactions were compromised at lower temperatures, attributable to the high activation energy required for the hydrogen atom abstraction by PINO. The addition of a Lewis acid catalyst (AlCl3) improves the product yield and reaction rate, possibly due to the formation of a PINO/AlCl3 complex which lowers the activation energy for hydrogen abstraction step.
Synthesis of 3-deoxy-2-uloses via the indium-mediated allylation reaction
Gintner, Manuel,Denner, Christian,Schm?lzer, Christoph,Fischer, Michael,Frühauf, Peter,K?hlig, Hanspeter,Schmid, Walther
, (2019)
Abstract: We utilized the indium-mediated allylation reaction for the synthesis of carbohydrate structures containing the 3-deoxy-2-ulose motif, a barely investigated compound class. The stereoselective outcome can be controlled by the presence or absence of a chelating group in α-position to the carbonyl function. By introduction of an UV-active allyl building block, we enabled epimer separation by HPLC towards the synthesis of 3-deoxy-d-glycero-d-galacto-2-nonulose, the carboxyl-reduced analogue of widely distributed 3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn). Ozonolysis of the introduced 2-C-methylidenepropan-1-ol motif provided the desired 3-deoxy-2-uloses. Graphical abstract: [Figure not available: see fulltext.].
Metal-free access to 3-allyl-2-alkoxychromanonesviaphosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols
Meng, Ling,Chang, Xiaoyong,Lin, Zhenyang,Wang, Jun (Joelle)
, p. 2663 - 2667 (2021)
A metal-free access to 3-allyl-2-alkoxychromanones by PPh3-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is described. This reaction is performed under mild conditions and it shows good functional group tolerance, providing a series of functionalized chromanones in moderate to high yields with excellent diastereoselectivities. Deuterium-labeling experiments to probe a possible mechanism and scale-up reaction were also conducted.
N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer
Xia, Qing,Tian, Hao,Dong, Jianyang,Qu, Yi,Li, Lili,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
, p. 9269 - 9273 (2018)
A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Br?nsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.
