18531-95-8Relevant articles and documents
Catalytic asymmetric benzidine rearrangement
De, Chandra Kanta,Pesciaioli, Fabio,List, Benjamin
, p. 9293 - 9295 (2013)
A chiral Br?nsted acid catalyzes the asymmetric benzidine rearrangement of N,N′-dinaphthylhydrazines. Different electronically and structurally diverse axially chiral 2,2′-binaphthyl diamine (BINAM) derivatives are obtained with high enantioselectivity. Copyright
New ligands for enantioselective recognition of chiral carboxylates based on 1,1′-binaphthalene-2,2′-diamine
Stibor, Ivan,Holakovsky, Roman,Mustafina, Asiya R.,Lhotak, Pavel
, p. 365 - 383 (2004)
Simple bis(arylureido)binaphthalenes and (arylamido)binaphthalenes have been synthesized in both racemic as well as optically active forms. One of these compounds has been found to complex chiral anions with modest enantioselectivity.
A simple and neutral receptor acting as a sensitive and switch-on fluorescent chemosensor for H2PO4-
Huang, Weiwei,Su, Hongyan,Yao, Sikai,Lin, Hai,Cai, Zunsheng,Lin, Huakuan
, p. 1697 - 1702 (2011)
A novel artificial anion chemosensor 1 based on 2, 2'-di (4-nitrophenylurea-β-N-yl) -1, 1'-binaphthyl is designed and synthesized for sensing anions including halide ions and oxoanions. The fluorescent emission of the binaphthyl of receptor 1, forming the hydrogen bonding with anions as the sensing mechanism, is monitored in DMSO for detecting anions. In brief, while most of the anion chemosensors are switch-off fluorescent chemosensor, or non-fluorescent sensor, receptor 1 exhibits obviously the switch-on emission during the complexation with H2PO4-. Springer Science+Business Media, LLC 2009.
Dilithium diamides [{Li(OC4H8)}2{C20H 12(NR)2}] (R = SMe3 or CH2But) derived from R-, S- or R,S-2,2′-diamino-1,1′-binaphthyl derivatives
Drost, Christian,Hitchcock, Peter B.,Lappert, Michael F.
, p. 3595 - 3601 (1996)
The dilithium diamides [{Li(thf)}2{C20H12(NR)2}] (R = SiMe3 1 or CH2But 2, thf = tetrahydrofuran) were prepared from R,S-2,2′-diamino-1,1′-binaphthyl, C20H12(NH2)2, via C20H12[N(H)SiMe3]2 or C20H12[NHC(O)But]2 and C20H12[N(H)CH2But]2, respectively, and were transformed into SiCl2[C20H12(NR)2] by treatment with SiCl4. The crystal structures of 1 and 2 were determined. They are monomers, having a Li(1)N(1)Li(2)N(2) buckled ring, with Li(1)-N(2) ca. 0.2 A shorter than Li(1)-N(1), the two groups R cis to one another, and N(1)-C(1) η2 bonded to Li(1). The R and S enantiomers were similarly prepared and their optical stability was demonstrated by their hydrolysis to R- and S-C20H12(NH2)2, respectively. Evidence is provided for the structures of [M{C20H12[N(SiMe3)]2}] (M = Ge or Sn), obtained by conversion of the stannylene into the crystallographically characterised [{Sn[(NSiMe3)2C20H12](μ-O)} 3].
Synthesis of Optically Active 2,2'-Dihalo-1,1'-binaphthyls via Stable Diazonium Salts
Brown, Kenneth J.,Berry, Matthew S.,Murdoch, Joseph R.
, p. 4345 - 4349 (1985)
Optically pure 2,2'-dibromo-1,1'-binaphthyl (DBBN) (5) and optically pure 2,2'-diiodo-1,1'-binaphthyl (DIBN) (6) are synthesized in preparative quantities starting from 2-naphthol.These compounds are useful for the preparation of chiral, bidentate ligands based on the 1,1'-binaphthyl system.The synthesis proceeds through a common optically active precursor, 2,2'-diamino-1,1'-binaphthyl ((R)-(+)-DABN) (2), and involves the preparation and subsequent decomposition of stable diazonium metal complexes (3 and 4).The effects of several variables, including the nature of the metal M, on these reactions is discussed, and comparison to related procedures reported in the literature is made.
Synthesis and Optical Properties of Axially Chiral Bibenzo[ b]carbazole Derivatives
Takishima, Ryo,Nishii, Yuji,Miura, Masahiro
, p. 1349 - 1354 (2021)
Pure organic materials with the circularly polarized luminescence (CPL) property have attracted significant research interest over the past few decades. In this study, a series of axially chiral bibenzo[b]carbazole derivatives were synthesized by adopting
A miniaturized analytical method based on molecularly imprinted absorbents for selective extraction of (S)-1,1′-binaphthyl-2,2′-diamine and combinatorial screening of polymer precursors by computational simulation
Xu, Xin,Huo, Feng,Zhu, Yongxia,Dong, Hongxing,Wang, Yanhui,Liu, Lijia,Zhang, Chunhong,Zhao, Fangbo
supporting information, p. 147 - 159 (2021/11/10)
Chiral resolution of binaphthylamine is often a toilful conundrum in the field of analytical chemistry and biomedicine. The work puts forward a selective, sensitive, and miniaturized analytical method based on molecularly imprinted polymers (MIPs) as adsorbent for miniaturized tip solid-phase extraction (MTSPE) in the separation of binaphthylamine enantiomer. This method combines the advantages of MIPs (high selectivity), MTSPE (low consumption), and high-performance liquid chromatography (HPLC, high sensitivity). A simple synthesis methodology of MIP (P2) was conducted through bulk polymerization with (S)-(?)-1,1′-binaphthyl-2,2′-diamine (S-DABN) as template together with methacrylic acid monomer, and ethylene glycol dimethacrylate as cross-linker in proper porogen, realizing a selective recognition and efficient enrichment for S-DABN. The method exhibited appreciable linearity (0.06–1.00 mg ml?1), low quantification limit (0.056 mg ml?1), good absolute recoveries (45.70%–69.29%), and high precision (relative standard deviations ≤ 3.54%), along with low consumption (0.50?ml sample solution and 25.0?mg adsorbent). Based on the density functional theory, computational simulation was used to make a preliminary prediction for rational design of MIPs and gave a reasonable elaboration involving the potential mechanism of templates interacting with functional monomers. The adsorption kinetics and thermodynamics were investigated to evaluate the recombination process of substrates. In addition, the selectivity of MIPs for S-DABN was obtained by MIP-MTSPE coupled with HPLC, which supports the feasibility of this convenient design process. The proposed method was employed for selective extraction of S-DABN and exhibited promising potential in the application of chiral analysis.
A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation
Jiang, Qianwen,Liu, Wei,Yang, Xiaoyu
supporting information, p. 23598 - 23602 (2020/10/23)
A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.
