10029-04-6Relevant articles and documents
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.
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.
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.
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.
Zinc-Mediated Double Addition on Functionalized Nitriles
Caillé, Julien,Pantin, Mathilde,Boeda, Fabien,Pearson-Long, Morwenna S.M.,Bertus, Philippe
, p. 1329 - 1341 (2019)
Allylzinc reagents were used to access highly functionalized tertiary carbinamine derivatives in high yields from cyanoesters and cyanocarbonates. While the monoaddition of organometallics on nitriles is generally observed, in this work the nucleophilic a
The aqueous trimethylamine mediated Baylis-Hillman reaction
Basavaiah, Deevi,Krishnamacharyulu, Marimganti,Rao, Anumolu Jaganmohan
, p. 2061 - 2069 (2000)
Aqueous trimethylamine mediated Baylis-Hillman coupling of alkyl acrylates with aldehydes is described.
Improved syntheses of ethyl α-(bromomethyl)acrylate and 2-methylene-1,3- propanediol via ethyl α-(hydroxymethyl)acrylate
Byun,Reddy,Bittman
, p. 1371 - 1374 (1994)
Ethyl α-(bromomethyl)acrylate (1) and 2-methylene-1,3-propanediol (2) have been prepared via formalhedyde addition to ethyl acrylate in the presence of DABCO, giving α, β-unsaturated ester 3. Reduction of hydroxy ester 3 with one equivalent of alane, then borohydride reduction of the resulting aldehyde 4 gives 2.
Phosphine-Catalyzed Cascade Annulation of MBH Carbonates and Diazenes: Synthesis of Hexahydrocyclopenta[c]pyrazole Derivatives
Guo, Hongchao,Li, Hongxiang,Liu, Hao,Shi, Wangyu,Wang, Chang,Wang, Wei,Wu, Yongjun
supporting information, p. 5571 - 5575 (2021/07/31)
A phosphine-catalyzed cascade annulation of Morita-Baylis-Hillman (MBH) carbonates and diazenes was achieved, giving tetrahydropyrazole-fused heterocycles bearing two five-membered rings in moderate to excellent yields. The reaction underwent an unprecedented reaction mode of MBH carbonates, in which two molecules of MBH carbonates were fully merged into the ring system.
An efficient and simple strategy toward the synthesis of highly functionalized compounds
Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi
, p. 978 - 995 (2021/08/06)
The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.
