[2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates:  Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes

Yamazaki, Shoko; Yanase, Yuichiro; Tanigawa, and Etsuko; Yamabe, Shinichi; Tamura, Hiroki

doi:10.1021/jo9911591

Cited by 21 publications

(10 citation statements)

References 31 publications

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“…1‐Phenyl‐2‐tosylpropan‐1‐one (4j): 25 White solid (30.5 mg, 53 %). 1 H NMR (400 MHz, CDCl 3 ): δ = 7.98 (d, J = 7.3 Hz, 2 H), 7.66 (d, J = 8.4 Hz, 2 H), 7.61 (t, J = 7.4 Hz, 1 H), 7.48 (t, J = 7.4 Hz, 2 H), 7.31 (d, J = 8.0 Hz, 2 H), 5.15 (q, J = 6.9 Hz, 1 H), 2.43 (s, 3 H), 1.56 (d, J = 6.9 Hz, 3 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Sulfonation and Trifluoromethylation of Enol Acetates with Sulfonyl Chlorides Using Visible‐Light Photoredox Catalysis

et al. 2013

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Section: Methodsmentioning

confidence: 99%

Sulfonation and Trifluoromethylation of Enol Acetates with Sulfonyl Chlorides Using Visible‐Light Photoredox Catalysis

et al. 2013

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“…General: Starting materials 4a , 4c , 4g − 4i , 4q , 4w − 4y , 8d , and 8e are commercially available. The following compounds were prepared according to literature procedures: 4b ,24 4f , 4v , 8c ,23 4j , 4k ,25 4l ,26 4m ,27 4n ,28 4o ,29 4p ,30 4r ,31 4s ,32 4t ,33 4u ,34 4z ,35 8a ,36 8b ,37 9a ,38 and 9b 39. Column chromatography was carried out using Merck SiO 2 60 with hexanes (PE, b.p.…”

Section: Methodsmentioning

confidence: 99%

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen

et al. 2003

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We report the metal‐catalyzed α‐hydroxylation of a variety of cyclic and acyclic β‐dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2‐propanol at ambient temperature. Most of the cyclic substrates 4a−4i give high yields of analytically pure products 5a−5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j−4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j−5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…The α-selenation of saturated sulfones or nitriles and subsequent oxidation and elimination has been previously reported as a strategy to generate vinyl sulfones [270][271][272][273] and acrylonitriles [274,275] respectively. However, there is no reported example of the α-selenation of the 1,3-sulfonylnitrile system required here.…”

Section: Development Of α-Selenation Conditionsmentioning

confidence: 99%

Kinetic Template‐Guided Tethering of Fragments

2012

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This thesis is composed of two separate projects: Kinetic Template-Guided Tethering of Fragments and Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1 Degradation after DNA Damage. Kinetic Template-Guided Tethering of FragmentsThe development of a novel methodology for the site-directed discovery of small molecule, protein-binding ligands is described. The protein of interest, with a cysteine thiol (either native or engineered) adjacent to the desired binding pocket, is incubated with mixtures of low molecular weight compounds (fragments) modified with either an acrylamide or a vinyl sulfonamide capture group. Any ligand within the mixture that binds within the pocket brings the capture group into close proximity with the cysteine thiol, promoting a conjugate addition reaction at an increased rate over the background reaction. The capture reaction is designed to be slow, such that during the time course of an experiment, no adduct formation is observed unless the reaction is templated by the protein. By this method, binding ligands are rapidly identified by mass spectrometry analysis of the crude reaction mixtures. The methodology has been termed 'kinetic template-guided tethering'. Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1Degradation after DNA Damage An inhibitor described within the literature was found to attenuate the reduction of cyclin D1 after DNA damage to cells. In order to implement a two-step chemical proteomics strategy to find the molecular target of this inhibitor, a synthesis of the compound with an alkyne appendage was required. The alkyne acts as a functional handle for attachment of a reporter molecule in cells via the Huisgen cycloaddition ('Click') reaction. The design and synthesis of this inhibitor with the alkyne appendage is described.

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[2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates: Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes

Cited by 21 publications

References 31 publications

Sulfonation and Trifluoromethylation of Enol Acetates with Sulfonyl Chlorides Using Visible‐Light Photoredox Catalysis

Sulfonation and Trifluoromethylation of Enol Acetates with Sulfonyl Chlorides Using Visible‐Light Photoredox Catalysis

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen

Kinetic Template‐Guided Tethering of Fragments

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