Day: August 10, 2021

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Ketalization reaction of racemic 1,3-alkanediols with l-menthone gave a mixture of diastereomeric spiroketals that was easily separated by silica gel column chromatography and converted into enantiomerically pure diols by acid-catalyzed hydrolysis.

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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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Fluorination followed by the Michael addition or Robinson annulation of 1,3-dicarbonyl compounds is introduced for the synthesis of acyclic and cyclic alpha-fluoro-beta-ketoesters and alpha-fluoro-1,3-diketones. The decarboxylation step can also be added to the reaction sequence. High efficiency is achieved by the microwave heating and atom economic one-pot synthesis.

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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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Rhodium(I) complexes of the new chiral ligand (2R,3R)-2,3-bis(diphenylphosphino)butane (4) – which is easily prepared from natural tartaric acid – hydrogenate alpha-(acylamino)acrylic acids to natural (S)-acylamino acids in high chemical (95-100percent) and optical (80-100percent) yields.

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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

Electric Literature of 4254-15-3, Modeling chemical reactions helps engineers virtually understand the chemistry, optimal size and design of the system, and how it interacts with other physics that may come into play. 4254-15-3, Name is (S)-Propane-1,2-diol, molecular formula is C3H8O2, belongs to chiral-oxygen-ligands compounds. In a Article，once mentioned of 4254-15-3

The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2lambda5-dioxaphospholanes (2) was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br; Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts.A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominatly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).

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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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Enantiopure (S,S) and (R,R) dimethyl-ethylenedithio-tetrathiafulvalene (DM-EDT-TTF) 1 donors are synthesized by cross coupling followed by decarboxylation reactions. In the solid state the methyl groups are arranged in axial positions within sofa-type conformation for the six-membered rings. Crystalline radical cation salts formulated as [(S,S)-1]2PF 6, [(R,R)-1]2PF6, and [(rac)-1] 2PF6 are obtained by electrocrystallization. When the experiment is conducted with enantioenriched mixtures both enantiopure and racemic phases are obtained. The monoclinic enantiopure salts, containing four independent donors in the unit cell, show semiconducting behavior supported by band structure calculations of extended Hueckel type. The racemic salt contains only one independent donor in the mixed valence oxidation state +0.5. Under ambient pressure the racemic material is metallic down to 120 K, while an applied pressure of 11.5 kbar completely suppresses the metal-insulator transition. Band structure calculations yield an open Fermi surface, typical for a pseudo-one-dimensional metal, with unperfected nesting, thus ruling out the possibility of charge or spin density modulations to be at the origin of the transition. Raman spectroscopy measurements, in agreement with structural analysis at 100 K, show no indication of low-temperature charge ordering in the racemic material at ambient pressure, thus suggesting Mott-type charge localization for the observed metal-insulator transition.

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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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For the role of monomeric metaphosphate and the nature of the transition states in the alcoholysis of phosphoric monoesters to be examined, phenyl <(R)-16O,17O,18O>phosphate and 2,4-dinitrophenyl <(R)-16O,17O,18O>phosphate have been synthesized and the stereochemical course of the methanolysis of phenyl phosphate monoanion and of dinitrophenyl phosphate dianion has been evaluated. <(R)-16O,17O,18O>Phosphocreatine has also been synthesized and the stereochemical course of the methanolysis of this molecule determined.In each case, complete inversion of configuration at phosphorus is observed.It is clear that metaphosphate, if it exists as a true intermediate in these reactions in protic solvent, does not leave the solvent cage in which it is generated.Indeed, product formation occurs more rapidly than rotation of the putative metaphosphate intermediate.These displacements must therefore occur by preassociative mechanisms in which there may be some assistance from the incoming nucleophile.The present results do not allow a distinction to be made between a “preassociative concerted” path (that is, an SN2-like displacement via a very loose transition state) and a “preassociative stepwise” path via a metaphosphate intermediate of very short lifetime.

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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

As a society publisher, everything we do is to support the scientific community – so you can trust us to always act in your best interests, and get your work the international recognition that it deserves. category: chiral-oxygen-ligands,

This study aimed to prepare robust immobilized epoxide hydrolase (EH) preparations for asymmetric hydrolysis of racemic epoxides such as styrene oxide, propylene oxide and epichlorohydrin. For this purpose, Aspergillus niger EH was immobilized onto Lewatit VP OC 1600 support by adsorption, modified Florisil and Eupergit C supports by covalently. The suitability of the supports was examined for protein binding capacity and rate of racemic styrene oxide hydrolysis. The protein-activity recovery yields were 75-85%, 82-78% and 90-75%, respectively for EH immobilized onto Lewatit VP OC 1600, modified Florisil and Eupergit C supports. All A. niger EH preparations catalyzed preferentially hydrolysis of (R)-epoxides. Although enantiomeric excess values of all the tested epoxides were 99%, the highest enantiopure epoxide yields were obtained as 48% for (S)-styrene oxide by the immobilized EHs onto modified Florisil and Eupergit C. The highest diol yield was obtained as 78% for 3-chloro-1,2-propanediol, however, its enantiomeric excess value was 28.2%. Enantioselectivity of A. niger EH was improved with the preparation of mentioned immobilized forms. The highest enantioselectivity value was obtained as 95 toward styrene oxide by A. niger EH immobilized onto modified Florisil . The results of reusability studies show that the immobilized EH preparations offer feasible potentials for the preparation of enantiopure epoxides than that of free form.

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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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Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68 %) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99 % ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76 %) and with moderate-to-high selectivities (up to 12:1 dr, up to 90 % ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts. Benzothiophenone and N-phenylrhodanine were successfully used as bis-nucleophiles in two enantioselective organocatalytic cascades. Their reactions with enals and dienones allowed the formation of new sulfur-containing spirocyclic scaffolds in good yields and with high selectivities. 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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The invention relates to a genetically modified lactic acid bacterium capable of producing (S,S)-2,3-butanediol stereo specifically from glucose under aerobic conditions. Additionally the invention relates to a method for producing (S,S)-2,3-butanediol and L-acetoin using the genetically modified lactic acid bacterium, under aerobic conditions in the presence of a source of iron-containing porphyrin or a source of metal ions (Fe3+/Fe2+). The lactic acid bacterium is genetically modified to express heterologous genes encoding enzymes catalysing the stereo-specific synthesis of (S,S)-2,3-butanediol; and additionally a number of genes are deleted in order to maximise the production of (S,S)-2,3-butanediol as compared to other products of oxidative fermentation.

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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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13C NMR, alone or in combination with 1H NMR, allows the assignment of the absolute configuration of chiral alcohols, amines, carboxylic acids, thiols, cyanohydrins, sec,sec-diols and sec,sec-aminoalcohols, derivatized with appropriate chiral auxiliaries. This extends the assignment possibilities of NMR to fully deuterated and to nonproton containing compounds.

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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