α-Methoxy-O-(N-arylcarbamoyl)oximes: synthesis and pharmacological activities

Gilly, Catherine; Taillandier, G.; Péra, MH; Luu‐Duc, C.; Demenge, Pierre; Catanho, M.T. de

doi:10.1016/s0223-5234(97)89090-3

Cited by 4 publications

(2 citation statements)

References 9 publications

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“…117 Remote alcohols do not interfere with hydration. 56 Propargyl ethers also hydrate well (Scheme 32), [205][206][207] and the reaction has often been used to prepare acetonyl ethers from propargyl ethers, like methoxy acetone 25e or higher derivatives. 206 Scheme 31 Synthesis of enantioenriched aldols by hydration.…”

Section: Scheme 27mentioning

confidence: 99%

Catalytic Hydration of Alkynes and Its Application in Synthesis

Hintermann¹,

Labonne²

2007

Synthesis

403

261

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The catalytic addition of water to alkynes (hydration) generates valuable carbonyl compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research has been devoted to finding catalysts based on less toxic metals, the most promising being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been realized in an efficient manner with ruthenium(II) complex catalysts. The present review article lists known hydration catalysts and discusses applications of catalytic hydration to different classes of substrates, with an emphasis on functional group tolerance and regioselectivity. 6 Reactions Related to Catalytic Alkyne Hydration 7 Conclusions and Outlook

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Section: Scheme 27mentioning

confidence: 99%

Catalytic Hydration of Alkynes and Its Application in Synthesis

Hintermann¹,

Labonne²

2007

Synthesis

403

261

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“…The silyl nucleophiles were synthesized by following known procedures: [(3,3-dimethylbut-1-en-2-yl)oxy]trimethylsilane, trimethyl[(1-phenylvinyl)oxy]silane, (cyclohex-1-en-1-yloxy)trimethylsilane, (cyclopent-1-en-1-yloxy)trimethylsilane, trimethyl(pent-2-en-3-yloxy)silane, 4-[(trimethylsilyl)oxy]pent-3-en-2-one . 3-Methoxy-3-methylbutan-2-one, 2-methoxy-2,4-dimethylpentan-3-one and 1-(1-methoxycyclohexyl)ethanone were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Bismuth(III) Triflate-Catalyzed Synthesis of Substituted 2-Alkenylfurans

Nitsch

Bach

2014

J. Org. Chem.

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A convergent synthesis of the title compounds is reported, which relies on a successive 2-fold SN'-type substitution reaction at methoxy-substituted propargylic acetates. The furan C3-C4 bond is presumably established by silyl enol ether attack at a propargylic cation intermediate. The resulting α-methoxyallene is intramolecularly substituted, leading to cyclization by displacement of the methoxy group (O-C2 bond formation) and to simultaneous formation of the exocyclic alkene double bond. Despite the relatively mild conditions, the reactions were complete within 5 min.

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Chiral Amine Synthesis – Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction

2010

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The review examines the chiral amine literature from 2000–2009 (May) concerning enantioselective and diastereoselective methods for N‐acylenamide and enamine reduction, reductive amination, and imine reduction. The reaction steps for each strategy, from ketone to primary chiral amine, are clearly defined, with best methods and yields for starting material preparation and final deprotection noted. Categories of chiral amines have been defined in Section 1 to allow the reader to quickly understand whether their specific target amine falls within a difficult to synthesize, or not, structural class. Amino acids are not considered in this work.

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α-Methoxy-O-(N-arylcarbamoyl)oximes: synthesis and pharmacological activities

Cited by 4 publications

References 9 publications

Catalytic Hydration of Alkynes and Its Application in Synthesis

Catalytic Hydration of Alkynes and Its Application in Synthesis

Bismuth(III) Triflate-Catalyzed Synthesis of Substituted 2-Alkenylfurans

Chiral Amine Synthesis – Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction

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