52776-14-4Relevant academic research and scientific papers
ARYLCYCLOHEXYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PSYCHIATRIC DISORDERS
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, (2021/07/02)
Provided herein are arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders.
The Silicon-Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones
List, Benjamin,Zhang, Pinglu,Zhou, Hui
, p. 1953 - 1956 (2021/11/17)
We have recently reported the strong and confined, chiral acid-catalyzed asymmetric 'silicon-hydrogen exchange reaction'. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.
Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions
Doppiu, Angelino,Goo?en, Lukas J.,Hu, Zhiyong,Pirkl, Nico,Sivendran, Nardana
supporting information, p. 25151 - 25160 (2021/10/19)
Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.
Aqueous chemoenzymatic one-pot enantioselective synthesis of tertiary α-aryl cycloketonesviaPd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation
Luan, Pengqian,Liu, Yunting,Li, Yongxing,Chen, Ran,Huang, Chen,Gao, Jing,Hollmann, Frank,Jiang, Yanjun
, p. 1960 - 1964 (2021/03/26)
An aqueous chemoenzymatic cascade reaction combining Pd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation (AH) was developed for enantioselective synthesis of tertiary α-aryl cycloketones in good yields and excellent enantioselectivities. The stereopreference of the enzyme in AH of α-aryl cyclohexenones was studied. An enantiocomplementary enzyme was obtained by site-directed mutation.
NMDA receptor antagonist and use thereof
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Paragraph 0412-0416, (2021/08/11)
The present invention relates to an NMDA receptor antagonist and use thereof. The NMDA receptor antagonist is a compound as shown in the formula I, and pharmaceutically acceptable salts, enantiomers, diastereoisomers, tautomers, solvates, isotope substitutes, polymorphic substances, prodrugs or metabolites thereof, and in the formula, ring A, ring B and R2 are as described in the specification. The invention also provides pharmaceutical compositions containing the compounds, and applications of the compounds in preparation of drugs for treating or preventing NMDA receptor mediated diseases.
Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl
He, Tianyu,Chen, Dengfeng,Qian, Shencheng,Zheng, Yu,Huang, Shenlin
supporting information, p. 6525 - 6529 (2021/09/02)
A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.
Thianthrenation-enabled α-arylation of carbonyl compounds with arenes
Huang, Yu-Hao,Nie, Xiao-Xue,Wang, Peng
supporting information, p. 7716 - 7720 (2020/11/02)
The Pd-catalyzed α-arylation of carbonyl compounds with simple arenes enabled by site-selective thianthrenation has been demonstrated. This onepot process using thianthrenium salts as the traceless arylating reagents features mild conditions and a broad substrate scope. In addition, this protocol could also tolerate the heterocyclic carbonyl compounds and complex bioactive molecules, which is appealing for medicinal chemistry.
Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis
Shevchenko, Grigory A.,Pupo, Gabriele,List, Benjamin
supporting information, p. 49 - 53 (2019/01/04)
Enantiopure α-hydroxy carbonyl compounds are common scaffolds in natural products and pharmaceuticals. Although indirect approaches towards their synthesis are known, direct asymmetric methodologies are scarce. Herein, we report the first direct asymmetric α-hydroxylation of α-branched ketones through enol catalysis, enabling a facile access to valuable α-keto tertiary alcohols. The transformation, characterized by the use of nitrosobenzene as the oxidant and a new chiral phosphoric acid as the catalyst, delivers a good scope and excellent enantioselectivities.
Enantioselective Protonation of Silyl Enol Ethers Catalyzed by a Chiral Pentacarboxycyclopentadiene-Based Bronsted Acid
An, Shaoyu,Li, Jun,Li, Pingfan,Yuan, Chao
supporting information, p. 1317 - 1320 (2019/06/19)
The enantioselective protonation of silyl enol ethers was realized in the presence of a pentacarboxycyclopenta-1,3-diene-based chiral Bronsted acid catalyst with water as an achiral proton source to give the corresponding α-aryl ketones in good yields and up to 75percent ee.
Ylide-Functionalized Phosphine (YPhos)-Palladium Catalysts: Selective Monoarylation of Alkyl Ketones with Aryl Chlorides
Hu, Xiao-Qiang,Lichte, Dominik,Rodstein, Ilja,Weber, Philip,Seitz, Ann-Katrin,Scherpf, Thorsten,Gessner, Viktoria H.,Goo?en, Lukas J.
supporting information, p. 7558 - 7562 (2019/10/02)
Ylide-functionalized phosphine (YPhos) ligands allow the palladium-catalyzed α-arylation of alkyl ketones with aryl chlorides with record setting activity. Using a cyclohexyl-substituted YPhos ligand, a wide range of challenging ketone substrates was efficiently and selectively monoarylated under mild conditions. A newly designed YPhos ligand bearing tert-butyl groups on the coordinating phosphorus atom is already active at room temperature. The synthetic potential was demonstrated by gram-scale reactions and the succinct synthesis of ?-caprolactone derivatives.
