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Chiral recognition of 1,1′-bi-2-naphthol enantiomers by twisted amidine derivatives: Rational design of a highly enantioselective receptor

Clarification of the molecular structures of diastereomeric complexes relevant to the enantioselective dual N¡¤¡¤¡¤HO bonding between the chiral C2 amidine derivative (S,S)-1 and 1,1′-bi-2-naphthol 2 in CDCl3 afforded the structural factor determining the sense of observed enantioselection. This insight into chiral recognition was successfully applied to the design of a new twisted dual hydrogen bond acceptor (S,S)-3 that exhibited a higher level of enantioselectivity toward 2.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Enantioselective oxidative coupling of 2-naphthol derivatives catalyzed by Camellia sinensis cell culture

Optically active 1,1?-binaphthyl-2,2?-diols were synthesized by oxidative coupling of 2-naphthols using Camellia sinensis cell culture as a catalytic system.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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(S)-2,2?-Bis(methoxymethoxy)[1,1?-binaphthyl]-3,3?- dicarbaldehyde

The two naphthalene rings of the title compound, C26H22O6, are in a transoid conformation. The dihedral angle between the mean planes of the naphthalene rings is large at 107.1 (3).

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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C,O-Chelated BINOL/Gold(III) Complexes: Synthesis and Catalysis with Tunable Product Profiles

Unprecedented stable BINOL/gold(III) complexes, adopting a novel C,O-chelation mode, were synthesized by a modular approach through combination of 1,1?-binaphthalene-2,2?-diols (BINOLs) and cyclometalated gold(III) dichloride complexes [(C^N)AuCl2]. X-ray crystallographic analysis revealed that the bidentate BINOL ligands tautomerized and bonded to the AuIII atom through C,O-chelation to form a five-membered ring instead of the conventional O,O?-chelation giving a seven-membered ring. These gold(III) complexes catalyzed acetalization/cycloisomerization and carboalkoxylation of ortho-alkynylbenzaldehydes with trialkyl orthoformates.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Discovery of (S)-[1,1′-Binaphthalene]-2,2′-diol

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 18531-99-2, molcular formula is C20H14O2, introducing its new discovery. Safety of (S)-[1,1′-Binaphthalene]-2,2′-diol

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-pi interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C-C and C-N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Synthesis, structure and catalysis of a NHC-Pd(II) complex based on a tetradentate mixed ligand

Bis-benzimidazolium salt (S)-2,2?-bis[2??-(N-picolyl-benzimidazoliumyl)ethoxy]-1,1?-binaphthyl hexafluorophosphate [(S)-LH2]¡¤(PF6)2 and its NHC palladium(ii) complex [(S)-LPd](PF6)2 (1) have been prepared and characterized. Complex 1 is formed by one tetradentate mixed ligand (S)-L and one Pd(ii) ion, in which one 15-membered ring and two 6-membered rings are present. In this complex, intramolecular pi-pi interactions between naphthalene rings and benzimidazole rings are observed. Additionally, the catalytic activity of complex 1 in three types of C-C coupling reactions (Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions) was investigated. The results show that complex 1 is an effective catalyst in these coupling reactions.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A than the horse prostaglandin preparation of key intermediate (by machine translation)

The invention relates to a horse prostaglandin II than for the preparation of a key intermediate, in particular, the present invention provides a first synthesis (S)- BINAL – H, and then the intermediate I in (S)- BINAL – H in the presence of the reduction than the key intermediate of […]. This method can be obtained and a metal purity intermediate II. The intermediates can be used for the synthesis of the material and a purity than horse prostaglandin. (by machine translation)

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Metal catalyst and ligand design,
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Chiral Polymers of Intrinsic Microporosity: Selective Membrane Permeation of Enantiomers

Following its resolution by diastereomeric complexation, 5,5?,6,6?-tetrahydroxy-3,3,3?,3?-tetramethyl-1,1?-spirobisindane (TTSBI) was used to synthesize a chiral ladder polymer, (+)-PIM-CN. (+)-PIM-COOH was also synthesized by the acid hydrolysis of (+)-PIM-CN. Following characterization, both (+)-PIM-CN and (+)-PIM-COOH were solvent cast directly into semipermeable membranes and evaluated for their ability to enable the selective permeation of a range of racemates, including mandelic acid (Man), Fmoc-phenylalanine, 1,1?-bi-2-naphthol (binol), and TTSBI. High ee values were observed for a number of analytes, and both materials exhibited high permeation rates. A selective diffusion?permeation mechanism was consistent with the results obtained with these materials. Their high permeability, processability, and ease of chemical modification offer considerable potential for liquid-phase membrane separations and related separation applications.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes

A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps. (Chemical Equation Presented).

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Metal catalyst and ligand design,
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Synthesis, Photo-physical and Electrochemical Properties of Dendrimers with (S)-BINOL Core and Benzothiazole Surface Unit

Chiral dendritic architectures with benzothiazole as surface group, 1,2,3-triazole as a bridging unit, and (S)-BINOL (1,1-bi-2-naphthol) as a core unit were synthesised in good yields via a convergent synthetic strategy. The chiroptical properties of the dendrimers revealed that the specific rotation increased in the order of dendrimers 4 > 3 > 2 > 1. All the dendrimers showed excellent optical and electrochemical response, and hence would find application in dye-sensitised solar cells.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI