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Thiophenophan-1-enes with chiral polyether bridges were prepared and their diastereospecific photochromic reactions were studied. The coupling reaction of substituted dithienylethenes and various chiral synthons afforded thiophenophan-1-enes, namely, bridged dithienylethenes, as single enantiomers without optical resolution, thus indicating that these reactions occurred diastereoselectively. Upon UV irradiation, each optically active thiophenophan-1-ene isomerized to the corresponding enantiomer of the closed form and returned to the initial enantiomer of the open form upon visible irradiation. Because thiophenophan-1-enes never isomerized to other diastereomers even at a high temperature, they underwent diastereospecific photochromic reactions. Large changes were observed in the measurement of the optical rotations of the solutions of thiophenophan-1-enes at 588 nm according to their photochromic reactions. As there was no absorption at this wavelength for both isomers of each thiophenophan-1-enes, the nondestructive readout of the photochromic reaction could be carried out by using these chiral thiophenophan-1-enes. Photo finish: Photochromic reactions of thiophenophan-1-enes with chiral polyether bridges occurred completely in a diastereospecific manner, even at high temperatures. Circular dichroism spectra and optical rotations changed photoreversibly according to the photochromic reactions between the enantiomers of the photoisomers (see figure). Copyright

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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COA of Formula: C3H8O2, Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 4254-15-3!

When developing chemical systems it’s of course important to gain a deep understanding of the chemical reaction process. COA of Formula: C3H8O2,

Acid-catalysed reaction of D-camphorquinone with racemic 1,2-diols (e.g. 3-chloropropane-1,2-diol) under kinetically controlled conditions yields a predominant diastereoisomeric acetal, that can be easily converted into an optically pure epoxide.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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1,2- and 1,3-Diols are readily protected as cyclic acetals and ketals through a graphene-catalyzed transacetalization process. The methodology features an atom economic procedure since quasi-stoichiometric conditions have been developed. Unlike prior systems, the graphene-catalyzed transacetalization is performed under Br°nsted and Lewis acid-free conditions and without solvent. Our method has been applied to several volatile compounds that are unsuitable for complex work-up and extensive purification steps. The very unusual catalytic properties of graphene for transacetalization reactions are ascribed to molecular charge transfer between graphene and substrates.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The potential utility of systematic synthetic strategy will be applicable to efficient generations of chemical libraries of compounds to find ‘hit’ molecules.Read on for other articles about 19132-06-0 . SDS of cas: 19132-06-0

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In the reaction of N,N-diethyl-alpha,alpha-difluorobenzylamine (DFBA) with 1,2- or 1,3-diols, selective mono-benzoylation occurs to afford mono-esters of the diols in good yield. The reaction is completed under mild conditions in a short reaction time. Further, prim-, sec-, and tert-diols and catechol can be converted to the corresponding mono-benzoates. DFBA is used for the protection of the hydroxy group in sugars. The selective mono-nicotinylation, formylation and pivaloylation of diols are also performed by using the corresponding difluoroalkylamines.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The triphenylmethyl group gives very simple access to the 1-protection of 1,2-diol as exemplified by racemic propane-1,2-diol. This group has, however, been shown to be incompatible with lipases commonly used for the resolution of alcohols. This turned out to be the case for Pseudomonas cepacia lipase, which we have used in our earlier work. Lipozyme, a Mucor miehei lipase, best known for 1,3-selectivity with glycerol is, however, shown to catalyze transacetylation onto the secondary hydroxyl group next to a triphenylmethoxy group. The transacetylation is completely enantioselective for the (R)-enantiomer giving a very simple method for the resolution of this type of 1,2-diol enantiomer.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 4254-15-3 is helpful to your research. Recommanded Product: 4254-15-3

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The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthesized from (alpha)-glycosides or the (beta) form respectively. Demercuration with chloride ion led to the insertion of a halo group adjacent to the new chiral center thus allowing for the possibility of further functionalization.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Compounds of formula IA or IB are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups and R1 is selected from straight or branched chain alkyl groups having from 1 to 8 carbon atoms; straight or branched chain alkenyl groups having from 2 to 8 carbon atoms; straight or branched chain hydroxy-substituted alkyl groups having from 1 to 8 carbon atoms; straight and branched chain hydroxy-substituted alkenyl groups having from 2 to 8 carbon atoms. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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We have analyzed the effects of mutations inserted during directed evolution of a specialized enzyme, Escherichia coli S-1,2-propanediol oxidoreductase (FucO). The kinetic properties of evolved variants have been determined and the observed differences have been rationalized by modeling the tertiary structures of isolated variants and the wild-type enzyme. The native substrate, S-1,2-propanediol, as well as phenylacetaldehyde and 2S-3-phenylpropane-1,2-diol, which are new substrates accepted by isolated variants, were docked into the active sites. The study provides a comprehensive picture of how acquired catalytic properties have arisen via an intermediate generalist enzyme, which had acquired a single mutation (L259V) in the active site. Further mutagenesis of this generalist resulted in a new specialist catalyst. We have also been able to relate the native enzyme activities to the evolved ones and linked the differences to individual amino acid residues important for activity and selectivity. F254 plays a dual role in the enzyme function. First, mutation of F254 into an isoleucine weakens the interactions with the coenzyme thereby increasing its dissociation rate from the active site and resulting in a four-fold increase in turnover number with S-1,2-propanediol. Second, F254 is directly involved in binding of aryl-substituted substrates via pi-pi interactions. On the other hand, N151 is critical in determining the substrate scope since the side chain amide group stabilizes binding of 1,2-substituted diols and is apparently necessary for enzymatic activity with these substrates. Moreover, the side chain of N151 introduces steric hindrance, which prevents high activity with phenylacetaldehyde. Additionally, the hydroxyl group of T149 is required to maintain the catalytically important hydrogen bonding network. A specialist enzyme, Escherichia coli propanediol oxidoreductase, was subjected to laboratory evolution with the purpose of broadening the substrate scope to include aryl-substituted alcohols and aldehydes. The wild-type enzyme displays very low and undetectable activity with phenylacetaldehyde and 3-phenyl-1,2-propanediol, respectively. Two rounds of directed evolution produced a variant enzyme displaying characteristics of a new specialist and others with traits of generalist enzymes.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Sep-21 News What I Wish Everyone Knew About 4254-15-3

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An efficient, highly enantioselective methodology for the synthesis of alpha-phosphanyl ketones 7 and 2-phosphanyl alcohols 12 and 13, important hemilable ligands for enantioselective homogeneous catalysis and chiral building blocks in general, has been developed. The key step of this first enantioselective synthesis of alpha-phosphanyl ketones is the diastereoselective phosphanylation of SAMP hydrazones 2 to produce alpha-phosphanyl hydrazones, isolated as the more stable borane adducts 6. Subsequent ozonolysis afforded alpha-phosphanyl ketones 7. The enantioselective synthesis of 2-phosphanyl alcohols 12 and 13 has been accomplished by two fundamentally different procedures: the phosphanylation of unsubstituted chiral aldehyde hydrazones 9 and the alkylation of alpha-diphenylphopshanyl acetaldehyde SAMP hydrazone 10. After separation of the minor diastereomer, the borane-protected alpha-phosphanyl aldehyde hydrazones 11 were converted to unprotected 2-phosphanyl alcohols 13 by ozonolysis, reduction and removal of the borane group. The absolute configuration of the functionalized phosphanes was determined by X-ray analysis, NOE experiments or polarimetry. VCH Verlagsgesellschaft mbH, 1997.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The design and synthesis of related molecules that are more effective, more selective, and less toxic than aspirin are important objectives of biomedical research.Keep reading other articles of 4254-15-3! Recommanded Product: (S)-Propane-1,2-diol

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Ligand exchange between 2 or RuCl23 and (R)- or (S)-BINAP produces BINAP-Ru(II) complexes which act as catalysts for the highly enantioselective hydrogenation of functionalized ketones.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate