Oxidative cyclization of .delta.,.epsilon.- and .epsilon.,.zeta.-unsaturated enol silyl ethers

Snider, Barry B.; Kwon, Taesoo

doi:10.1021/jo00303a005

Cited by 82 publications

(21 citation statements)

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“…[20,21] Cyclisation and loss of a proton provides [4]ferrocenophane radical 14 and then keto-alcohol 4, after further one-electron oxidation and trapping with water. When the deuterium-labelled bis- To probe this reaction mechanism in more detail, we investigated the reaction of vinyl ferrocene [22] under our optimised conditions, postulating that a range of oxygenated products might be obtained in the absence of a second vinyl substituent.…”

Section: Resultsmentioning

confidence: 99%

Reaction of 1,1′‐Divinyl Ferrocene with One‐Electron Oxidants: Entry into Functionalised [4]Ferrocenophanes and Observation of an Isotope‐Dependent Chemoselectivity Effect

Gleixner

Joly

Tremayne

et al. 2010

Chemistry A European J

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1,1'-Divinyl ferrocene (2) reacts with K(3)[Fe(CN)(6)] under basic biphasic conditions to give a [4]ferrocenophane (4) in good yield. Incorporating deuterium labels into the internal positions of the vinyl groups of 2 affects the chemoselectivity of the reaction; thus under identical reaction conditions, [D(2)]-2 reacts to provide a diol-functionalised [4]ferrocenophane, [D(2)]-D/L-6 in addition to the expected keto-alcohol, [D(1)]-4. Variants on this one-electron oxidative cyclisation methodology can be used to give other [4]ferrocenophanes; thus, the reaction of 2 with CuCl(2) in MeOH or iPrOH leads to dialkoxy [4]ferrocenophanes 19 and 20, respectively, whereas the reaction of 2 with benzyl carbamate in the presence of tBuOCl gives a bis(carbamate)[4]ferrocenophane, 21. Mechanisms to account for the formation of the products, the stereoselectivity, and the unusual isotope-dependent chemoselectivity in the reaction of 2 and [D(2)]-2 with K(3)[Fe(CN)(6)] are proposed.

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Section: Resultsmentioning

confidence: 99%

Reaction of 1,1′‐Divinyl Ferrocene with One‐Electron Oxidants: Entry into Functionalised [4]Ferrocenophanes and Observation of an Isotope‐Dependent Chemoselectivity Effect

Gleixner

Joly

Tremayne

et al. 2010

Chemistry A European J

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“…72 2-Hydroxy-1-naphthoic acid esters (and amides) of type 57 were synthesized by the CAN promoted cyclization of 5-aryl-3-oxopentanoic acid ester (or amide) 55 (Scheme 10). 73 Hydroxyalkyl substituted cyclopropylsulfides underwent single electron-transfer oxidation mediated by CAN affording cyclic ethers and spirocyclic compounds.…”

Section: Intramolecular Carbon-carbon Bond Forming Reactionsmentioning

confidence: 99%

Recent advances in CAN mediated reactions in organic synthesis

Nair

Deepthi

2009

Tetrahedron

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“…Ceric ammonium nitrate (CAN) is the best known and most widely used oxidant of lanthanide reagents [163]. Early oxidations with CAN had been carried out in strongly acidic media using stoichiometric quantities of the reagent.…”

Section: Scheme 74 Scheme 75mentioning

confidence: 99%