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Selective mono-acylation of 1,2- and 1,3-diols using (alpha,alpha- difluoroalkyl)amines

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£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

The important role of 1,5-Diphenylpenta-1,4-dien-3-one

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Iridium-Catalyzed Cyclization of Isoxazolines and Alkenes: Divergent Access to Pyrrolidines, Pyrroles, and Carbazoles

A heterogeneous iridium-complex-catalyzed N-O-cleaving rearrangement/cyclization of 2,3-dihydroisoxazoles with alkenes has been developed. It provides divergent access to multiple substituted pyrrolidines, pyrroles, and carbazoles. The iridium catalyst remains highly catalytic active after seven cycles. The gram-scale synthesis afforded a carbazole with strong bluish-violet fluorescence.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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<1,4> Addition of (Methylthio)methyl p-Tolyl Sulfone to alpha,beta-Unsaturated Carbonyl Compounds

The lithio derivative of (methylthio)methyl p-tolyl sulfone (1) reacted with various alpha,beta-unsaturated carbonyl compounds to afford <1,4> adducts in good to high yields.The introduced (methylthio)(p-tolylsulfonyl)methyl group was easily converted to a (methylthio)carbonyl group or a formyl group.When the reaction of 1 with methyl acrylate using sodium hydride as a base was performed in DMF at an ambient temperature,2-(methoxycarbonyl)-4-(methylthio)-4-(p-tolylsulfonyl)cyclohexanone (8) was obtained in 81 percent yield.Furthermore, 8 was shown to be an important intermediate for preparing 2-substituted 2-(methoxycarbonyl)-1,4-cyclohexanediones.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Top Picks: new discover of (S)-Propane-1,2-diol

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Stereocontrolled Reduction of 2-Acyl-1,3-oxathiane Derivatives by Zn(BH4)2 and YCl3-NaBH4

Both enantiomers of 1,2-alkanediols were prepared by the diastereocontrolled reduction of ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; reduction with Zn(BH4)2 selected one diastereoface to give one diastereomer and that with YCl3-NaBH4 produced another diastereomer selectively.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Some scientific research about (S)-Propane-1,2-diol

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Kinetic Resolution of 1,2-Diols with D-Camphorquinone; Preparation of (R)-(Chloromethyl)oxirane

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£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Brief introduction of (S)-Propane-1,2-diol

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A concise stereoselective total synthesis of Botryolide B

The first total synthesis of Botryolide B is described from easily accessible starting materials. The synthetic strategy involves Jacobsen resolution, Sharpless epoxidation, Swern oxidation, Yamaguchi reaction, and ring closing metathesis (RCM).

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Properties and Exciting Facts About (S)-Butane-1,3-diol

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Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols

Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Synthesis, in vitro biological activities and in silico study of dihydropyrimidines derivatives

We describe here the synthesis of dihydropyrimidines derivatives 3a-p, and evaluation of their alpha-glucosidase enzyme inhibition activities. Compounds 3b (IC50 = 62.4 ¡À 1.5 muM), 3c (IC50 = 25.3 ¡À 1.26 muM), 3d (IC50 = 12.4 ¡À 0.15 muM), 3e (IC50 = 22.9 ¡À 0.25 muM), 3g (IC50 = 23.8 ¡À 0.17 muM), 3h (IC50 = 163.3 ¡À 5.1 muM), 3i (IC50 = 30.6 ¡À 0.6 muM), 3m (IC50 = 26.4 ¡À 0.34 muM), and 3o (IC50 = 136.1 ¡À 6.63 muM) were found to be potent alpha-glucosidase inhibitors in comparison to the standard drug acarbose (IC50 = 840 ¡À 1.73 muM). The compounds were also evaluated for their in vitro cytotoxic activity against PC-3, HeLa, and MCF-3 cancer cell lines, and 3T3 mouse fibroblast cell line. All compounds were found to be non cytotoxic, except compounds 3f and 3m (IC50 = 17.79 ¡À 0.66-20.44 ¡À 0.30 muM), which showed a weak cytotoxic activity against the HeLa, and 3T3 cell lines. In molecular docking simulation study, all the compounds were docked into the active site of the predicted homology model of alpha-glucosidase enzyme. From the docking result, it was observed that most of the synthesized compounds showed interaction through carbonyl oxygen atom and polar phenyl ring with active site residues of the enzyme.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Regio-, Diastereo-, and Enantioselective Synthesis of Vicinal Diols via alpha-Silyl Ketones

A new versatile and efficient regio-, diastereo-, and enantioselective synthesis of vicinal diols s-trans-4, s-trans-5, and s-cis-4 is described.Symmetrical ketones are converted into their SAMP- or RAMP-hydrazones which are then silylated with (isopropyloxy)dimethylsilyl chloride, followed by ozonolysis to afford the alpha-silyl ketones (R)-2 of high enantiomeric purity (ee 90 > 98percent).On the other hand, methyl ketones, after conversion into the corresponding (-)-(S)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP) hydrazones, are silylated and then alkylated with R1 to afford unsymmetrical alpha-silyl ketones (S)-3 of high enantiomeric purity (ee 90->98percent).The reduction of the above obtained alpha-silyl ketones with L-Selectride, followed by oxidative cleavage of the C-Si bond gives rise to s-trans-4, s-trans-5, and s-cis-4 with high diastereoselectivity (de 95->98percent) and without racemization (ee >90->98percent).

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Boronic compounds

This invention relates to a diboron derivative of formula (I) or a diboron derivative of formula (II) or a diboron derivative of formula (III) where R1, R2, R3 and R4 are each independently selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, a group of the formula ?(R5Q)mR6 where Q is selected from O, S, NR7, optionally substituted arylene and optionally substituted cycloalkylene, m is an integer selected from 1 to 3, the or and each R5 is independently an optionally substituted C1-C3 alkylene, R6 is C1-C3 alkyl or hydrogen, and R7 is hydrogen or C1-C12 alkyl; each X is independently selected from O, S(O)n and NR7, where n is an integer from 0 to 3, R7 is hydrogen or C1-C12 alkyl, or one or more of ?NR1R7, ?NR2R7, ?NR3R7 and ?NR4R7 represent an optionally substituted 5 or 6 membered heterocyclyl group,and A, A1 and A2 are divalent groups which may or may not be different.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate