352533-60-9Relevant academic research and scientific papers
Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
Krieck, Sven,Lange, Markus,Schüler, Philipp,Vilotijevic, Ivan,Westerhausen, Matthias,Zi, You
supporting information, p. 575 - 580 (2020/03/27)
Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization
SUBSTITUTED DIHYDROPYRAZOLO PYRAZINE CARBOXAMIDE DERIVATIVES
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Page/Page column 113, (2020/01/10)
The invention relates to substituted dihydropyrazolo pyrazine carboxamide derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and diabetes, and also urogenital and ophthalmic disorders.
Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates
Formánek, Bed?ich,?imek, Michal,Kamlar, Martin,Císa?ová, Ivana,Vesely, Jan
, p. 907 - 920 (2019/02/10)
An organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90-96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45-73%) and high optical purity (82-99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.
Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles
Zi, You,Lange, Markus,Schultz, Constanze,Vilotijevic, Ivan
supporting information, p. 10727 - 10731 (2019/07/09)
Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i
Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization
Cui, Hai-Lei,Jiang, Lu,Tan, Hao,Liu, Si
supporting information, p. 4772 - 4780 (2019/10/28)
We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1-a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita-Baylis-Hillman carbonates (up to 96% yield)
Employing Small Polyfunctionalized Molecules for a Diastereoselective Synthesis of Highly Substituted Indolines
de Souza Fernandes, Fábio,Cormanich, Rodrigo A.,Zeoly, Lucas A.,Formiga, André Luiz B.,Coelho, Fernando
, p. 3211 - 3223 (2018/07/06)
An efficient approach has been developed for the diastereoselective synthesis of 1,2,3-trisubstituted indolines. The reaction sequence includes the highly diastereoselective reductive amination of 2-oxo-1,3-propanediols, which are prepared by postfunctionalization of Morita–Baylis–Hillman (MBH) adducts, to give substituted 2-amino-1,3-propanediols with an anti relative configuration. A subsequent intramolecular palladium-catalyzed Buchwald coupling reaction provided the 1,2,3-trisubstituted indolines in 47–82 % yield. The preference for the anti diastereomer was investigated by Gibbs free energy diagrams and applying theoretical calculations at the M06–2X/6-31+G** level.
Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
supporting information, p. 13441 - 13445 (2018/09/21)
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
α-ZrP/Uracil/Cu2+ nanoparticles as an efficient catalyst in the Morita-Baylis-Hillman reaction
Hajipour, Abdol R.,Zakery, Saedeh
, (2018/09/06)
A facile synthesis of uracil-Cu2+ nanoparticles immobilized on alpha-zirconium hydrogen phosphate (α-ZrP), abbreviated as α-ZrP/Uracil/Cu2+, was presented. This compound was synthesized by the thermal method and used as a reusable ca
Organocatalyzed Decarboxylative Trichloromethylation of Morita–Baylis–Hillman Adducts in Batch and Continuous Flow
Enevoldsen, Martin V.,Overgaard, Jacob,Pedersen, Maja S.,Lindhardt, Anders T.
supporting information, p. 1204 - 1208 (2018/02/06)
Two protocols for the organocatalyzed decarboxylative trichloromethylation of Morita–Baylis–Hillman (MBH) substrates have been developed. Applying sodium trichloroacetate, as the trichloromethyl anion precursor, in combination with an organocatalyst and a
Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles: Via novel [3 + 2] annulation of isoindigos and MBH carbonates
Ren, Hong-Xia,Peng, Lin,Song, Xiang-Jia,Liao, Li-Guo,Zou, Ying,Tian, Fang,Wang, Li-Xin
supporting information, p. 1297 - 1304 (2018/03/06)
A novel and diastereoselective [3 + 2] annulation of isoindigos and Morita-Baylis-Hillman carbonates has been developed for the highly efficient and one-step preparation of highly steric dispiro[cyclopent-3′-ene]bisoxindoles with two all-carbon quaternary
