88335-92-6Relevant academic research and scientific papers
Photocatalyzed, β-Selective Hydrocarboxylation of α,β-Unsaturated Esters with CO2under Flow for β-Lactone Synthesis
Kang, Guowei,Romo, Daniel
, p. 1309 - 1315 (2021/02/01)
A photocatalyzed, β-selective hydrocarboxylation of α,β-unsaturated esters employing CO2 radical anion generated under flow conditions was developed. A range of substrates bearing a variety of functional groups were tolerated, demonstrating chemoselectivity. A series of quaternary carboxylic acids were obtained from sterically demanding β,β-disubstituted alkenes including those derived from natural products. Mechanistic studies support a Giese-type CO2 radical anion conjugate addition followed by hydrogen atom transfer from (TMS)3SiH as the principal reaction pathway. Finally, a telescoped process involving the described β-carboxylation followed by a α-bromination/β-lactonization sequence provides a strategy for β-lactone synthesis.
Synthesis method of trans 1 and 2 - cyclohexane dicarboxylic acid monomethylester
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Paragraph 0044-0048; 0049-0053, (2021/08/25)
The invention provides a synthesis method of trans 1 and 2 - cyclohexane dicarboxylic acid monomethylester, and belongs to the field of organic synthesis. The trans 1-2 -cyclohexane dicarboxylic acid monomethylester synthesis method comprises the following steps: trans-cyclohexane -1 and 2 -dicarboxylic acid anhydride. The methanol and solvent is added to the reaction vessel, stirred and purified to obtain the target product trans 1, 2 - cyclohexanedicarboxylate, wherein the solvent is any one or more of tetrahydrofuran, 2 - methyltetrahydrofuran, benzene, toluene, methylene chloride, chloroform, ethyl acetate, methyl acetate or diethyl ether. Since a specific solvent is selected for the reaction solvent, racemization does not occur in the process of synthesizing trans 1 and 2 - cyclohexane dicarboxylic acid monomethyl ester, and the trans ee and 1 cyclohexane dicarboxylic acid monomethyl ester with higher 2 - value can be finally obtained.
Ionic Liquid Gels: Supramolecular Reaction Media for the Alcoholysis of Anhydrides
Rizzo, Carla,Mandoli, Alessandro,Marullo, Salvatore,D'Anna, Francesca
, p. 6356 - 6365 (2019/05/24)
The search of new enantioselective catalysts, able to promote synthetically useful organic reactions with high levels of asymmetric induction, should be associated with the attention to the suitable reaction medium able to achieve the best efficiency in c
Remote conformational responses to enantiomeric excess in carboxylate-binding dynamic foldamers
Eccles, Natasha,Le Bailly, Bryden A.F.,Della Sala, Flavio,Vitórica-Yrezábal, I?igo J.,Clayden, Jonathan,Webb, Simon J.
supporting information, p. 9331 - 9334 (2019/08/08)
A crystallographically characterised zinc(ii)-capped foldamer can sense the enantiomeric excess of scalemic carboxylate solutions, including those produced by enantioselective organocatalysis, and can relay this input signal along the foldamer body to a remote glycinamide group, which then provides an NMR spectroscopic output.
Synthesis of trans-fused octahydroisoindole-1-carboxylic acids
Laborda, Pedro,Sayago, Francisco J.,Cativiela, Carlos,Gotor, Vicente
, p. 404 - 411 (2018/05/22)
trans-Fused octahydroisoindole-1-carboxylic acids are bicyclic proline analogues of potential interest in the search for new drugs. Within this work, the trans-fused octahydroisoindole system has been constructed using methyl trans-2-(hydroxymethyl)cycloh
Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
Xu, Lingjun,Han, Shuwen,Yan, Linjie,Wang, Haifeng,Peng, Haihui,Chen, Fener
supporting information, p. 309 - 317 (2018/02/19)
A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.
Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of meso Cyclic Anhydrides
Yan, Lin-Jie,Wang, Hai-Feng,Chen, Wen-Xue,Tao, Yuan,Jin, Kai-Jun,Chen, Fen-Er
, p. 2249 - 2253 (2016/07/19)
The synthesis of new chloramphenicol-base-derived thiourea organocatalysts, (1S,2R)-12 a–f and (1R,2R)-15 a–c, and their use in the enantioselective alcoholysis of meso-anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)-12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)-15 a–c. This technique was used to synthesize (R)-(?)-baclofen.
Synthesis of cinchona alkaloid sulfonamide polymers as sustainable catalysts for the enantioselective desymmetrization of cyclic anhydrides
Takata, Shohei,Endo, Yuta,Shahid Ullah, Mohammad,Itsuno, Shinichi
, p. 72300 - 72305 (2016/08/09)
The Mizoroki-Heck polymerization of cinchona-based sulfonamide dimers and aromatic diiodides was investigated in the presence of a palladium catalyst, to obtain chiral polymers in high yields. An iodobenzenesulfonamide derivative of a cinchona alkaloid was also polymerized via self-polycondensation under the same reaction conditions. The catalytic activities of these chiral polymers were examined by using them as catalysts in the enantioselective desymmetrization of cyclic anhydrides.
Desymmetrization of acid anhydride with asymmetric esterification catalyzed by chiral phosphoric acid
Yamada, Ken-ichi,Oonishi, Akinori,Kuroda, Yusuke,Harada, Shingo,Kiyama, Hiroki,Yamaoka, Yousuke,Takasu, Kiyosei
, p. 4098 - 4100 (2016/08/18)
Asymmetric desymmetrization of σ-symmetric acid anhydrides was achieved with chiral phosphoric acid as a Br?nsted acid catalyst. The key of success was finding of benzhydrol and 2,2-diphenylethanol as the nucleophiles of choice. The corresponding half esters were obtained in good yields with high selectivity.
Monomeric and Dimeric 9-O Anthraquinone and Phenanthryl Derivatives of Cinchona Alkaloids as Chiral Solvating Agents for the NMR Enantiodiscrimination of Chiral Hemiesters
Uccello Barretta, Gloria,Mandoli, Alessandro,Balzano, Federica,Aiello, Federica,De Nicola, Beatrice,Del Grande, Alessandro
, p. 693 - 699 (2015/10/12)
Mono- and bis-alkaloid chiral auxiliaries with anthraquinone or phenanthryl cores were probed as chiral solvating agents (CSAs) for the enantiodiscrimination of chiral cyclic hemiesters. The dimeric anthraquinone derivative and the monomeric phenanthryl o
