1033605-25-2Relevant articles and documents
Synthesis of a rigidified bicyclic AAZTA-like ligand and relaxometric characterization of its GdIII complex
Martinelli, Jonathan,Martorana, Enrico,Tei, Lorenzo
supporting information, (2020/11/04)
The synthesis of a novel constrained polydentate ligand CpAAZTA derived from the heptadentate polyaminocarboxylic ligand AAZTA (6-amino-6-methylperhydro-1,4-diazepine-N, N’,N’’,N’’-tetraacetic acid) in which the ethylene bridge of the 1,4-diazepine ring i
Highly regioselective ring-opening of epoxides with amines: A metal- A nd solvent-free protocol for the synthesis of β-amino alcohols
Li, Dong,Wang, Jing,Yu, Shibo,Ye, Silei,Zou, Wenjie,Zhang, Hongbin,Chen, Jingbo
supporting information, p. 2256 - 2259 (2020/03/04)
We herein report a metal- A nd solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines. This process provides β-amino alcohols in high yields with excellent regioselectivity. Importantly, this epoxide ring-opening protocol can be used for the introduction of amines in natural products during late-stage transformations.
Chiral Titanium Coordination Assemblies: Robust Cooperative Self-Supported Catalysts for Asymmetric Ring Opening of meso-Epoxides with Aliphatic Amines
Sun, Zheming,Chen, Jiangbo,Liu, Yaoqi,Tu, Tao
, p. 494 - 505 (2017/02/10)
By utilizing the oxygen bridge in dimeric μ-oxo-titanium-salen complexes as an efficient cross-linkage, a series of robust chiral titanium coordination assemblies has been successfully fabricated with the ditopic bridging ligands derived from BINOL and salen derivatives via coordination polymerization, which are fully characterized by IR, elemental analysis, XRD and microscopic studies. Because of their insolubility in most organic solvents and water, these metal-organic assemblies can successfully function as robust self-supported chiral catalysts, allowing an asymmetric ring opening (ARO) of meso-epoxides with aliphatic amines. Remarkably, owing to the linkage effects and the cooperation of two kinds of chiral titanium moieties in the metal-organic assemblies, the self-supported chiral catalysts demonstrate extremely high stability. They not only show high tolerance towards various meso-epoxides and nucleophilic aliphatic amines, but also can be reused in more than 20 runs without obvious metal leaching and loss in yields and enantioselectivities. Furthermore, the self-supported catalyst accomplished a one-pot tandem olefin epoxidation and ARO of an epoxide sequence starting from the olefin, 30% hydrogen peroxide and benzylamine. In marked contrast, the reaction failed to work when using the two corresponding homogeneous catalysts under identical reaction conditions. Good yields and enantioselectivities were obtained by the robust self-supported catalyst, which clearly indicates the cooperative effects between two chiral moieties within the metal-organic assemblies. The two catalytic centers can perform their own duties without interference and this further supports our strategy for the self-supported catalyst design. (Figure presented.).
Synthesis of bicyclic proline derivatives by the aza-Cope-Mannich reaction: Formal synthesis of (±)-acetylaranotin
Belov, Dmitry S.,Ratmanova, Nina K.,Andreev, Ivan A.,Kurkin, Alexander V.
supporting information, p. 4141 - 4147 (2015/10/19)
Herein we suggest an approach to oxygenated bicyclic amino acids based on an aza-Cope-Mannich rearrangement. Seven distinct amino acid scaffolds analogous to the natural products were prepared on a gram scale with precise control of stereochemistry. Successful implementation of our strategy resulted in the formal synthesis of acetylaranotin.
Substituted Imidazopyridines as HDM2 Inhibitors
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Paragraph 0816, (2014/07/08)
The present invention provides substituted imidazopyridines as described herein or a pharmaceutically acceptable salt or solvate thereof. The representative compounds are useful as inhibitors of the HDM2 protein. Also disclosed are pharmaceutical compositions comprising the above compounds and potential methods of treating cancer using the same.
Heterogeneous Lewis acid catalysis with self-organized polymeric rare earth arylsulfonates under solvent-free conditions
Furuno, Hiroshi,Ishida, Shuichi,Suzuki, Shoko,Hayano, Tetsuji,Onitsuka, Satoaki,Inanaga, Junji
experimental part, p. 1007 - 1018 (2010/10/03)
Polymeric rare earth arylsulfonates, easily prepared from rare earth triisopropoxides and biphenyl-4,4'-disulfonic acid (BPDSA) or 1,3,5-triphenylbenzene trisulfonic acid (TPTSA) in a self-organization manner, were found to work as an efficient heterogene
Microwave-enhanced sulphated zirconia and SZ/MCM-41 catalyzed regioselective synthesis of β-amino alcohols under solvent-free conditions
Negron-Silva, Guillermo,Hernandez-Reyes, C. Xochitl,Angeles-Beltran, Deyanira,Lomas-Romero, Leticia,Gonzalez-Zamora, Eduardo
, p. 977 - 985 (2008/09/18)
A solvent-free approach for the regioselective synthesis of β-amino alcohols in shorter reaction times and higher yields, compared to conventional heating is described. It involves microwave (MW) exposure of undiluted reactants in the presence of sulphated zirconia (SZ) or sulphated zirconia over MCM-41 (SZM) as catalyst. Both acid materials can be easily recovered and reused.
Comparative study of the regioselective synthesis of β-aminoalcohols under solventless conditions catalyzed by sulfated zirconia and SZ/MCM-41
Negron-Silva, Guillermo,Hernandez-Reyes, C. Xochitl,Angeles-Beltran, Deyanira,Lomas-Romero, Leticia,Gonzalez-Zamora, Eduardo,Mendez-Vivar, Juan
, p. 2515 - 2532 (2008/03/15)
Sulfated zirconia and SZ/MCM-41 were used as catalysts for the synthesis of β-aminoalcohols via epoxide aminolysis. Sulfated zirconia was prepared by sol-gel and SZ/MCM-41 was obtained by impregnation. Solid catalysts were characterized by XRD, SEM-EDS, UV-Vis, FT-IR pyridine desorption and Nitrogen physisorption. Both acid materials were useful as catalysts, even when they were recycled several times. The β-aminoalcohols were characterized by FT-IR, 1H- and 13C-NMR and GC-MS.
Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis
Schiffers, Ingo,Rantanen, Toni,Schmidt, Frank,Bergmans, Werner,Zani, Lorenzo,Bolm, Carsten
, p. 2320 - 2331 (2007/10/03)
A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.
Syntheses and X-Ray Crystal Structures of Tricyclic Ketones Containing Trans-Fused Azabicyclooctane Units
Mori, Miwako,Saitoh, Fumihiko,Uesaka, Noriaki,Okamura, Kimio,Date, Tadamasa
, p. 4993 - 4998 (2007/10/02)
Tricyclic ketones containing the trans-fused 3-azabicyclooctane framework were prepared from the reactions of dienes and Cp2ZrBu2, followed by treatment with carbon monoxide.The structures were confirmed by X-ray analysis.
