Oxidative Rearrangement of Cyclic Tertiary Allylic Alcohols with IBX in DMSO

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Abstract

A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.

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This article has been cited by 9 ACS Journal articles (5 most recent appear below).

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  IBS-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxone

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  Regioselective Heck Vinylation of Electron-Rich Olefins with Vinyl Halides: Is the Neutral Pathway in Operation?

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  TEMPO/NaIO₄−SiO₂: A Catalytic Oxidative Rearrangement of Tertiary Allylic Alcohols to β-Substituted α,β-Unsaturated Ketones

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    The novel catalytic method for the oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated ketones is described. TEMPO/NaIO4−SiO2 causes facile and efficient oxidative rearrangement of various acyclic substrates as well as ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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