- Asymmetric synthesis of 2-aryl-5-oxotetrahydrofuran-2-carboxylic acids
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3-Aryl-2-hydroxycyclopent-2-en-1-ones, when subjected to asymmetric oxidation, result in enantiomerically enriched 2-aryl-5-oxotetrahydrofuran-2- carboxylic acids. Electron-donating substituents in the para position of the phenyl ring increase the yield and decrease the enantioselectivity of the process. Georg Thieme Verlag Stuttgart.
- Jogi, Artur,Paju, Anne,Pehk, Tonis,Kailas, Tiiu,Mueuerisepp, Aleksander-Mati,Kanger, Tonis,Lopp, Margus
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p. 3031 - 3036
(2008/02/08)
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- Isomerisation of primary propargyl alcohols to vinyl ketones mediated by Hg(OAc)2
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Mercuric acetate mediated isomerisation of primary propargyl alcohols to vinyl ketones analagous to Rupe rearrangement is described.
- Yadav,Prahlad,Muralidhar
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p. 3415 - 3418
(2007/10/03)
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- Conjugate Addition of Acyloxy Groups to Alkynylphenyliodonium Tetrafluoroborates under Both Basic and Acidic Conditions. Synthesis of α-Acyloxy Ketones
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Reaction of alkynylphenyliodonium tetrafluoroborates 1 with sodium salts of carboxylic acids in the presence of water affords α-acyloxy ketones.The reaction also proceeds under acidic conditions.The fact that the reaction of (4-hydroxy-1-butynyl)phenyliod
- Ochiai, Masahito,Kunishima, Munetaka,Fuji, Kaoru,Nagao, Yoshimitsu
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p. 4038 - 4041
(2007/10/02)
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- Silyl Nitronates in Organic Synthesis. Routes to Heterocycles and Cyclopentanoids. Synthesis of Allethrolone and Calythrone. Acylation and Cyanohydroxylation of Double Bonds. An Exploratory Study
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Silyl nitronates are versatile reagents for the preparation of heterocycles by dipolar addition to double bonds.The intermediate isoxazolidines can be transformed to 2-isoxazolines, isoxazoles, furans, dihydrofuranones, pyrazoles, pyridazines and pyridazones.Reduction of 2-isoxazolines with Ti3+ leads to hydroxylated 1,4-diketones, which subsequently can be cyclized to cyclopentenones.Routes to calythrone, rethrolones, prostanoids and a number of naturally occurring dihydrofuranones are devised, as well as synthetic procedures for acylation, preparation of endiones, hydroxyacylation, cyanation and hydroxycyanation of double bonds.
- Andersen, Soeren H.,Das, Nalin B.,Joergensen, Ruth D.,Kjeldsen, Gunhild,Knudsen, Jes S.,et al.
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- ADDITION VON ALDEHYDEN AN AKTIVIERTE DOPPELBINDUNGEN, XXVII. MITTEILUNG : EIN EINFACHER WEG ZU 2-HYROXY-CYCLOPENTENONEN
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A new, easy synthetic route to 2-hydroxy-3-alkyl-cyclopentenones starting from the thiazolium salt catalyzed addition of aldehydes to 1-acetoxy-3-buten-2-one is described.
- Stetter, H.,Schlenker, W.
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p. 3479 - 3482
(2007/10/02)
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