14439-71-5Relevant articles and documents
New generation of nucleophilic glycine equivalents
Ellis, Trevor K.,Ueki, Hisanori,Soloshonok, Vadim A.
, p. 941 - 944 (2005)
A new generation of nucleophilic glycine equivalents, designed to contain a functional framework, that allows control over the physical properties as well as the reactivity, is described. The reactivity of these nucleophilic glycine equivalents have been compared to previously described examples with the application of various transformations such as alkyl halide alkylations, Michael additions, and aldol condensations.
Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand
Liu, Feng,Wu, Na,Cheng, Xu
supporting information, p. 3015 - 3020 (2021/05/05)
Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.
Synthesis of trifluoromethyl substituted nucleophilic glycine equivalents and the investigation of their potential for the preparation of α-amino acids
Bergagnini-Kolev, Mackenzie,Howe, Mitchell,Burgess, Emily,Wright, Payton,Hamburger, Samantha,Zhong, Zhennan,Ellis, Shawna B.,Ellis, Trevor K.
supporting information, (2020/12/02)
The synthetic preparation of several Ni(II) complexed Schiff Bases of glycine will be introduced, as well as investigations into their reactivity and utility. Key to these investigations is the incorporation of electron-withdrawing trifluoromethyl groups within the framework of the conjugated system that stabilizes the enolate derived from the glycine component. Reactivity was evaluated for each of the complexes under phase transfer catalyzed alkylations with hydroxide bases, as well as the DBU catalyzed Michael Additions of optically active 3′-substituted-2-oxazoladinone amides of unsaturated carboxylic acids. It was found that the trifluoromethyl containing nucleophilic glycine equivalents were more reactive than their non-trifluoromethyl analogues in both reaction types. Therefore, the application of these modified Ni(II) complexes of glycine Schiff Bases are useful for the preparation of α-amino acids through phase transfer catalyzed alkylation as well as the preparation of optically pure β-substituted pyroglutamic acid precursors.
TRICYCLIC CRBN LIGANDS AND USES THEREOF
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Paragraph 0776; 0777, (2020/01/24)
The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin
Abdelkafi, Hajer,Michau, Aurélien,Pons, Valérie,Ngadjeua, Flora,Clerget, Alexandra,Ait Ouarab, Lilia,Buisson, David-Alexandre,Montoir, David,Caramelle, Lucie,Gillet, Daniel,Barbier, Julien,Cintrat, Jean-Christophe
, p. 8114 - 8133 (2020/09/21)
High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.
Chromatographic approach to study the configurational stability of Ni(II) complexes of amino-acid Schiff bases possessing stereogenic nitrogen
Han, Jianlin,Jean, Marion,Roussel, Christian,Moriwaki, Hiroki,Soloshonok, Vadim A.
, p. 328 - 335 (2019/02/06)
Herein, we disclose the design of a model Ni(II) complex of glycine Schiff base possessing single-nitrogen stereogenic center, which was successfully used for high-performance liquid chromatography (HPLC)-assisted assessment of its configurational stability. The major finding is that the configurational stability of the Ni(II)-coordinated nitrogen is profoundly dependent on the reaction conditions used, in particular the solvent, and can range from inconsequential (t? less than 5?min) to virtually completely stable (t? 90?y). The discovery reported in this study most likely to be of certain theoretical and synthetic value.
Effect of substituents on the configurational stability of the stereogenic nitrogen in metal(II) complexes of α-amino acid Schiff bases
Mei, Haibo,Jean, Marion,Albalat, Muriel,Vanthuyne, Nicolas,Roussel, Christian,Moriwaki, Hiroki,Yin, Zizhen,Han, Jianlin,Soloshonok, Vadim A.
supporting information, p. 401 - 409 (2019/04/01)
Herein, we report a general method for quantitative measurement of the configurational stability of the stereogenic nitrogen coordinated to M (II) in the corresponding square planar complexes. This stereochemical approach is quite sensitive to steric and electronic effects of the substituents and shown to work well for Ni(II), Pd(II), and Cu(II) complexes. Structural simplicity of the compounds used, coupled with high sensitivity and reliability of experimental procedures, bodes well for application of this approach in evaluation of chemical stability and stereochemical properties of newly designed chiral ligands for general asymmetric synthesis of tailor-made amino acids.
NH-type of chiral Ni(ii) complexes of glycine Schiff base: Design, structural evaluation, reactivity and synthetic applications
Bergagnini, MacKenzie,Fukushi, Kazunobu,Han, Jianlin,Shibata, Norio,Roussel, Christian,Ellis, Trevor K.,Acena, Jose Luis,Soloshonok, Vadim A.
, p. 1278 - 1291 (2014/03/21)
The work being reported here deals with the design of a new type of "N-H" Ni(ii) complexes of glycine Schiff bases and study general aspects of their reactivity. It was confirmed that the presence of NH function in these Ni(ii) complexes does not interfere with the homologation of the glycine residue, rendering these derivatives of high synthetic value for the general synthesis of α-amino acids. In particular, the practical application of these NH-type complexes was demonstrated by asymmetric synthesis of various-substituted pyroglutamic acids via Michael addition reactions with chiral Michael acceptors.
Substituent-controlled preference of carbonyl group-metal coordination in d8 metal complexes with non-symmetric pentadentate ligands. Structural and stereochemical aspects
Han, Jianlin,Ono, Taizo,Uekusa, Hidehiro,Klika, Karel D.,Soloshonok, Vadim A.
, p. 5375 - 5381 (2014/04/03)
Chirally switchable Ni(ii) and Pd(ii) complexes were synthesized and fully characterized by X-ray crystallography and additionally by spectroscopic means (NMR and MS). The syntheses and characterization of their ligands are also reported. It was found that control of the stereochemical preference between (S*,S*) and (S*,R*) diastereomers by substituent modification of the ligand sidearms was possible in the solid state with the preferred atomic coordinations of the sidearms consistent with expectations based on the electron-withdrawing properties of the substituent -o-CF 3 group. The dilemma arising in terms of assigning the absolute configuration descriptors resulting from selecting between strictly following only the covalent bonds of the ligand and disregarding the nature of the bonds altogether and thus bringing the coordinate bonds into consideration to determine the stereochemical priority sequence is hereby resolved by declaring that the latter option is to be preferred. The results obtained here provide a clear indication that sidearm substitution of the Ni(ii) and Pd(ii) complexes need not disturb macromolecular stereochemical arrangements leading to quasidiastereomeric relationships. This permits the design of molecular systems sensitive to external stimuli with predictable macromolecular structure. This journal is the Partner Organisations 2014.
Design and synthesis of molecules with switchable chirality via formation and cleavage of metal-ligand coordination bonds
Soloshonok, Vadim A.,Ueki, Hisanori,Moore, Jason L.,Ellis, Trevor K.
, p. 3512 - 3513 (2007/10/03)
Here we describe a design and synthesis of organic molecules with switchable central chirality via simple cleavage and formation of metal-ligand coordination bonds, as a potentially useful and conceptually new approach to the design of a new generation of organic chiroptical molecular switches. Copyright
