Synthesis of Novel Bifunctional Michael Acceptors

Ring-closing olefin metathesis (RCM) of 4-methylene-1,7-octadien-3-ones 2, followed by isomerization of the carbon--carbon double bond of 6-methylene-2-cyclohexenones 3 from exo to endo, produced various phenols 4. As an application of the method, the RCM/Mizoroki-Heck reaction of 2 was proven to be also effective for the synthesis of phenols having an additional substituent at ortho-benzylic position.

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Synthesis of Substituted Phenols by Using the Ring‐Closing Metathesis/Isoaromatization Approach

Yoshida

Narui

Imamoto

2008

Chemistry A European J

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Synthesis of Novel Bifunctional Michael Acceptors.

Urbaneja

Krause

2005

ChemInform

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Solvent‐Free Carbon–Oxygen Bond Formation Catalysed by CeCl₃·7 H₂O/NaI: Tetrahydropyranylation of Hydroxy Groups

et al. 2006

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An efficient and highly chemoselective method fo the protection of free hydroxy compounds with 3,4‐dihydro‐2H‐pyran is reported. Since the deprotection of THP‐ethers occurs very readily at room temperature, the successful use of this type of protecting group depends only upon how readily it can be introduced. For this we have examined the tetrahydropyranylation of alcohols and phenols catalysed by the CeCl3·7 H2O/NaI system surface under solvent‐free conditions. The reaction presents the advantage of being performable under extremely mild conditions by use of catalytic amounts of an interesting Lewis acidic system consisting of the CeCl3·7 H2O/NaI catalyst combination, which can be easily separated from the reaction mixture. The advantages of this procedure, which utilizes cheap and “friendly” reagents, over the previously reported ones are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Synthesis of Novel Bifunctional Michael Acceptors

Cited by 6 publications

References 20 publications

Synthesis of Substituted Phenols by Using the Ring‐Closing Metathesis/Isoaromatization Approach

Synthesis of Substituted Phenols by Using the Ring‐Closing Metathesis/Isoaromatization Approach

Synthesis of Novel Bifunctional Michael Acceptors.

Solvent‐Free Carbon–Oxygen Bond Formation Catalysed by CeCl₃·7 H₂O/NaI: Tetrahydropyranylation of Hydroxy Groups

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Synthesis of Novel Bifunctional Michael Acceptors

Cited by 6 publications

References 20 publications

Synthesis of Substituted Phenols by Using the Ring‐Closing Metathesis/Isoaromatization Approach

Synthesis of Substituted Phenols by Using the Ring‐Closing Metathesis/Isoaromatization Approach

Synthesis of Novel Bifunctional Michael Acceptors.

Solvent‐Free Carbon–Oxygen Bond Formation Catalysed by CeCl3·7 H2O/NaI: Tetrahydropyranylation of Hydroxy Groups

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Product

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Solvent‐Free Carbon–Oxygen Bond Formation Catalysed by CeCl₃·7 H₂O/NaI: Tetrahydropyranylation of Hydroxy Groups