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Treatment of bis(o-nitrophenyl)disulfides 1 with SmI2 led to simultaneous reduction of nitro groups and reductive cleavage of S-S bonds as well as the formation of the active intermediates 2. The intermediates 2 reacted smoothly with aldehydes or ketones, acid chlorides or anhydrides, alpha-bromoketones, and alpha,beta-unsaturated ketones at room temperature to afford the desired benzothiazolines 3, benzothiazoles 4, 2H-1,4-benzothiazines 5, and 2,3-dihydro-1,5-benzothiazepines 6, respectively, in moderate to high yields under mild and neutral 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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A set of bioinspired carbamoyl CNP pincer complexes are reported that are relevant to [Fe]-hydrogenase (Hmd). The dicarbonyl species [(CNHNNHPR2)Fe(CO)2I] [R = Ph, 1; R = iPr, 2] undergoes ligand deprotonation, resulting in the dearomatized complexes of formulas [(CNHNN=PR2)Fe(CO)2] (5 and 6). The crystal structure and 1H{31P} NMR spectroscopy of the iodide-bound dearomatized species [Na(18-crown-6)][(CNHNN=PPh2)Fe(CO)2I] (7) showed that the deprotonated moiety was the phosphoramine N(H) linkage. Separately, the monocarbonyl complexes [(CNHNNHPR2)Fe(CO)(MeCN)2](BF4) (8 and 9) synthesized, as well as deprotonated and dearomatized in similar fashion. Reactivity studies revealed that the parent dicarbonyl complexes require more forceful conditions for H2 activation, compared with the monocarbonyl complexes. The ligand backbone was not found to participate in H2 activation and H2 ? hydride transfer to an organic substrate was not observed in either case. Density functional theory calculations revealed that the higher reactivity of the monocarbonyl complex in H2 splitting could be attributed to its higher affinity for H2. This behavior is attributed to two key points related to the requisite dI(Fe) ? sigma*(H2) back-bonding interaction in a conventional M-H2 Kubas interaction: (i) generally, the weaker pidonor capacity of the dicarbonyls, and (ii) specifically, the detrimental effect of a strongly piacidic CO ligand (versus weakly piacidic MeCN ligand) trans to the H2 activation site. The higher reactivity of the monocarbonyl complex is also evidenced by the catalytic transfer hydrogenation by monocarbonyl 8, whereas dicarbonyl 1 was ineffective. Overall, the results suggest that Nature uses the dicarbonyl motif in [Fe]-hydrogenase to diminish the interaction between the Fe center and dihydrogen, thereby preventing premature H2 activation prior to substrate (H4MPT+) binding and any resulting nonspecific hydride transfer reactivity.

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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 the dual peroxisome proliferator-activated receptor (PPAR) gamma/delta agonist (R)-3-{4-[3-(4-chloro-2-phenoxy-phenoxy) -butoxy]-2-ethyl-phenyl}-propionic acid (20) for the treatment of type 2 diabetes and associated dyslipidemia is described. The compound possesses a potent dual hPPAR gamma/delta agonist profile (IC50 = 19 nM/4 nM; EC50 = 102 nM/6 nM for hPPARgamma and hPPARdelta, respectively). In preclinical models, the compound improves insulin sensitivity and reverses diabetic hyperglycemia with less weight gain at a given level of glucose control relative to rosiglitazone.

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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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(S)-2-Methyloxetane (1) and its precursor (S)-1,3-butanediol (2) were prepared in low to moderate chemical yield with less than 0.5percent racemization from (S)-ethyl lactate (4) and from (2S,3S)-allothreonine (14b).For the first time the enantiomeric purities of both the starting material and the product (1) were carefully determined by high-precision capillary gas chromatography on optically active resolving stationary phases.The validity of the quadrant rule, correlating the relative configuration of alkyloxiranes with the order of elution from manganese(II) bis<(1R)-3-(heptafluorobutyryl)camphorate> (3) by complexation gas chromatography, is also confirmed for 2-methyloxetane (1).

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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 asymmetric catalytic synthesis of naturally occurring and biologically active spiro compounds is a challenge for modern chemical methodology. Here we report the construction of spiro compounds through cascade [5+1] double Michael reactions between divinyl ketones and N-unprotectedoxindoles or N-phenyl-protected pyrazolones catalyzed by a combination of the easily available 9-amino-9-deoxy-epi-quinine with N-Boc-D-phenylglycine. The desired multistereogenic spiro[cyclohexanone-oxindoles and -pyrazolones] were obtained with high yields (up to 98 %) andstereoselectivities (up to >20:1 dr, 99 % ee). An efficient approach to spiro compounds through cascade [5+1] double Michael reactions between divinyl ketones and oxindoles or N-protected pyrazolones in the presence of 9-amino-9-deoxy-epi-quinine and N-Boc-D-phenylglycine is reported. Multistereogenic spiro[cyclohexanone- oxindoles and -pyrazolones] are obtained with high yields (up to 98 %) and stereoselectivities (up to >20:1 dr, 99 % ee). 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 regioselectivity of cyclodehydration of chiral diols has been examined with the reagents diethoxytriphenylphosphorane, triphenylphosphine-tetrachloromethane-potassium carbonate, and triphenylphosphine-diethyl azodicarboxylate. (S)-(+)-Propane-1,2-diol and (R)-(-)-pentane-1,4-diol afford 80-87percent retention of stereochemistry at the chiral carbon in the ether while (S)-(+)-phenylethane-1,2-diol affords essentially racemic styrene oxide with all three reagents.

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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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Marine-derived species, in particular, fungi, algae, sponges, and coelenterates are fertile grounds for the discovery of biologically and pharmacologically potent compounds. These molecules are structurally unique and possess a wide range of pharmacological activities. The rigid spiroacetal framework, that is, tetrahydro-spirofurofuranones is present in cephalosporolides E, F, H, and I, while the macrolactone structure is exemplified by cephalosporolides B, C, D, G, and J. These marine-derived molecular architectures are appealing to the synthetic community for their stereoselective synthesis. The present review represents a comprehensive overview of all the reported syntheses of these marine-derived molecules.

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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 report the syntheses and crystal structures of novel organotin chloride complexes with functional organic substituents from HSnCl3· 2Et2O (1-3). Whereas Cl3SnCHPhCH2C(O)(CH) 2Ph (1) was synthesized in a traditional route from HSnCl 3·2Et2O and dibenzylideneacetone, C 6H5Cl5O4Sn2 (2) and C8H9Cl5O4Sn2 (3) represent products of a condensation reaction of mononuclear organotintrichlorides that comprise both C=C and C=O functional groups and additionally exhibit characteristic intramolecular donor-acceptor interactions. Due to the condensation, compounds 2 and 3 combine SnCl2 with SnCl3 groups within one molecule. 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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Microwave-assisted stereoselective 1,3-dipolar cycloaddition of C,N-diarylnitrones (i.e., N-(arylmethylidene)benzenamine N-oxides) 2 to substituted bis(arylmethylidene)acetones (=1,5-diarylpenta-1,4-dien-3-ones) 1 leading to diastereoisomer pairs of bis-isoxazolidines 3 and 4 in good to excellent yield is described (Scheme2 and Table2). The configuration outcome of the reaction is discussed based on the NMR and X-ray data of the products. 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 synthetic methods of trifluoromethylated cyclopentadienes/fulvenes/ norbornenes have been developed using 3-CF3-1,4-dien-3-ols as the synthons, which can be easily prepared by the regiospecific 1,2-addition of the Ruppert-Prakash reagent (TMSCF3) to divinyl ketones. All the reactions are carried out under mild, metal-free conditions to afford the corresponding products in high to excellent 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