Recent progress on using BINOLs in enantioselective molecular recognition

Sheng, Yu; Pu, Lin

doi:10.1016/j.tet.2014.11.007

Cited by 70 publications

(33 citation statements)

References 131 publications

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“…[1][2][3][4] Therefore, in the pharmaceutical, agrochemical, food and fragrance industries, chiral discrimination has become increasingly important to ensure the quality of the end products and to eliminate incorrect administration of undesired enantiomers with harmful activities. 13,14 Until now, a wide variety of chiral fluorescent sensors have been reported using not only small molecules, such as binaphthyl-, 15, 16 1,8-diheteroarylnaphthalene-, 17,18 helicene- 19 and bis(oxazolinyl)phenol-based compounds, 20 but also synthetic macromolecules. [5][6][7][8][9][10][11][12] Among them, using fluorescence responses as output signals is considered to be one of the most powerful techniques for chiral discrimination owing to its easy, rapid, sensitive and high-throughput features.…”

Section: Introductionmentioning

confidence: 99%

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

et al. 2016

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Chiral fluorescent sensors were designed and synthesized from naturally occurring optically active cellulose, in which a terthienyl moiety was used as a fluorescent signaling unit, and their chiral recognition abilities were investigated on the basis of an enantioselective fluorescence response to aromatic nitro compounds as quenchers. A cellulose phenylcarbamate derivative (Ce-1b) exhibited an apparent enantioselectivity for various types of aromatic nitro compounds containing either central or axial chirality. Considering the fact that a corresponding monosaccharide derivative showed almost no enantioselectivity, the chiral recognition ability of the cellulose-based fluorescence sensor is attributed to its regular higherorder structures, probably a one-handed helical conformation. The resolution ability of Ce-1b as a chiral stationary phase for high-performance liquid chromatography was basically higher than that of the previously reported cellulose tris( phenylcarbamate), revealing that the terthienyl-based pendant provides attractive chiral recognition sites along the helical backbone as well as the fluorescent functionality. † Electronic supplementary information (ESI) available. See

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Section: Introductionmentioning

confidence: 99%

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

et al. 2016

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“…As it was emphasized in the introduction, these compounds are very interesting as fluorescent probes for chiral recognition applications, since they show a very intense fluorescence emission and chirality. Thus, it is important to gain some insight on the fluorescence emission of these materials.…”

Section: Resultsmentioning

confidence: 99%

“…Amongst the possible chiral synthons commercially available, the 1,1′‐bis‐2‐naphthol chiral derivative (BINOL), firstly synthesized by von Ritcher in 1873, may be considered one of the most attractive chiral building blocks to promote the modification of CNTs walls, due to the recognized applications of this molecule, either as enantioselective fluorescent sensors for molecular recognition or in asymmetric catalysis . Furthermore, BINOL backbones chirality and its strong fluorescence emissions make these molecules attractive enantioselective fluorescent sensors for chiral recognition . Recently, Akazaki et al.…”

Section: Introductionmentioning

confidence: 99%

(S)‐BINOL Immobilized onto Multiwalled Carbon Nanotubes through Covalent Linkage: A New Approach for Hybrid Nanomaterials Characterization

et al. 2015

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(S)-6-(4-(Methoxycarbonyl)phenyl)-1,1'-bis-2-naphthol, ac hiral 1,1'-bis-2-naphthol (BINOL) derivative, wasp repared via SuzukiC ÀCc oupling and immobilized onto diamine-functionalized multiwalled carbonn anotubes. The BINOL was first derivatized with ac arboxylic acid, capable of forming an amide linkage with the amine-carbon nanotube modified surface. The 4-methoxyphenylboronic acid was replaced by 3-fluoro-4-(methoxycarbonyl)phenylboronic acid and (S)-6-(3-fluoro-4-(methoxycarbonyl)phenyl)-1,1'-bis-2-naphthol was obtained and used as ap robe to better quantify the organic material. It was found that in the hybrid material, 1/3 of amine groups have been transformed into the corresponding amide (S)-BINOL derivative. The chemical and electronic integrity of the chiral BINOL ligand is maintained after the ligand immobilization. Evaluation in diethyl zinc and Ti(OiPr) 4 -catalyzed alkylation of benzaldehyde showed that both methoxycarbonylphenyl andf luoromethoxycarbonylphenyl BINOL moieties do not significantly influence the catalytic activity or selectivity of the process. However,w hen hybridm aterials were used, similar activities were obtained, but with lower enantioselectivities.T his result could be due to ac ompetitive alkylation reactiono ccurring on the carbon surfaceo rb yt he constraint caused by the ligand proximity on the support surface.

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“…Hence, efficient enantioselective methods for their syntheses have attracted considerable developmental attention . Typically, optically active BINOLs are synthesized by enzymatic or chemical resolution of racemic substrates ,. In addition, the enantioselective oxidative couplings of 2‐naphthol derivatives catalyzed by chiral, non‐racemic copper, iron, and vanadium complexes provides a more direct and atom‐economical route to C 2 ‐symmetric BINOLs .…”

Section: Methodsmentioning

confidence: 99%

Lipase‐Catalyzed Dynamic Kinetic Resolution of C₁‐ and C₂‐Symmetric Racemic Axially Chiral 2,2′‐Dihydroxy‐1,1′‐biaryls

2018

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We have discovered that the racemization of configurationally stable,a xially chiral 2,2'-dihydroxy-1,1'biaryls proceeds with ac atalytic amount of ac yclopentadienylruthenium(II) complex at 35-50 8 8C. Combining this racemization procedure with lipase-catalyzed kinetic resolution led to the first lipase/metal-integrated dynamic kinetic resolution of racemic axially chiral biaryl compounds.T he method was applied to the synthesis of various enantio-enriched C 1 -and C 2 -symmetric biaryl diols in yields of up to 98 %and enantiomeric excesses of up to 98 %, which paves the way for new developments in the field of asymmetric synthesis.

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Recent progress on using BINOLs in enantioselective molecular recognition

Cited by 70 publications

References 131 publications

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

(S)‐BINOL Immobilized onto Multiwalled Carbon Nanotubes through Covalent Linkage: A New Approach for Hybrid Nanomaterials Characterization

Lipase‐Catalyzed Dynamic Kinetic Resolution of C₁‐ and C₂‐Symmetric Racemic Axially Chiral 2,2′‐Dihydroxy‐1,1′‐biaryls

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Recent progress on using BINOLs in enantioselective molecular recognition

Cited by 70 publications

References 131 publications

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

(S)‐BINOL Immobilized onto Multiwalled Carbon Nanotubes through Covalent Linkage: A New Approach for Hybrid Nanomaterials Characterization

Lipase‐Catalyzed Dynamic Kinetic Resolution of C1‐ and C2‐Symmetric Racemic Axially Chiral 2,2′‐Dihydroxy‐1,1′‐biaryls

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Lipase‐Catalyzed Dynamic Kinetic Resolution of C₁‐ and C₂‐Symmetric Racemic Axially Chiral 2,2′‐Dihydroxy‐1,1′‐biaryls