Oxidative coupling of 2-substituted 1,2-dihydro-1-naphthols using Jones reagent: a simple entry into 3,3′-disubstituted 1,1′-binaphthyl-4,4′-diols

Fillion, Eric; Trepanier, Vincent E.; Mercier, Lauren G.; Remorova, Anna A.; Carson, Rebekah

doi:10.1016/j.tetlet.2004.12.099

Cited by 9 publications

(10 citation statements)

References 23 publications

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“…En route to 15 , nucleophilic ring opening of oxacyclobutane with (3-isopropyl-2-(methoxymethyl)-1-phenyl)lithium furnished the corresponding 3-aryl-1-propanol. The precursors to 14 and 17 were synthesized from the parent benzaldehyde via stabilized Wittig olefination and hydrogenation, followed by ester reduction (Scheme b) . The 1-propanol derivatives were then converted to bromides and homologated with lithium (trimethylsilyl)acetylide to the corresponding alkynylsilane.…”

Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

et al. 2009

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A full account of the Pd-catalyzed intramolecular reactions of (E)-2,2-disubstituted 1-alkenyldimethylalanes with aryl triflates as an entry into polycarbocyclic structures displaying an ethyl−methyl-substituted all-carbon benzylic quaternary center is herein presented. It was found that the efficiency of the Pd-catalyzed carbon−carbon bond forming process is highly affected by the structure of the starting material, including tether length and aryl substitution pattern; substituting the position ortho to the triflate is mandatory to obtain a good yield of the carbocycle. Moreover, the formation of 1-ethyl-1-methylindanes is facile in comparison to the case for the analogous tetrahydronaphthalenes, for which the competing methyl cross-coupling reaction is equally competent. It was established through labeling studies that the carbon−carbon bond forming events are stereospecific and proceed though the intermediacy of a neopentylic sp3-gem-dimetallic palladio(II) dialkylaluminoalkane species, from which a 1,2-methyl migration from aluminum to carbon occurs. Intramolecular palladium-catalyzed reactions of 1-naphthyl triflates with (E)-2,2-disubstituted 1-alkenyldimethylalanes revealed two competing reaction pathways: arylation with sequential 1,2-alkyl migration from aluminum to carbon and intramolecular 1,2-diarylation, in which the catalytic cycle is terminated by direct arylation of the C(sp3)−Pd(II) bond. Factors such as tether length, additives, solvent polarity, and C−H···Pd interactions between the Pd(II) center and the hydrogen atom at the 8-position all influence not only the pathway taken by the (σ-aryl)palladium(II) complexes but also the subsequent reactivity of the (σ-alkyl)palladium(II) complexes.

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Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

et al. 2009

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“…Hepten-3-one was obtained through oxidation of 1-hepten-3-ol (Aldrich) with Jones’ reagent . A glass ampule containing 1-hepten-3-one (112 mg, 1 mmol) and hydroquinone (2 mg) was flushed with nitrogen, sealed, and placed in an oil bath at 180 °C for 3 h .…”

Section: Methodsmentioning

confidence: 99%

“…Hepten-3-one was obtained through oxidation of 1-hepten-3-ol (Aldrich) with Jones' reagent. 18 A glass ampule containing 1-hepten-3-one (112 mg, 1 mmol) and hydroquinone (2 mg) was flushed with nitrogen, sealed, and placed in an oil bath at 180 °C for 3 h. 19 The ampule was opened, taking care to cool the system with EtOH and dry ice. The unreacted 1-hepten-3-one was removed through evaporation at room temperature, while filtration removed crystals of hydroquinone, yielding 1 (63.9 mg, 57.1%).…”

Section: General Experimental Proceduresmentioning

confidence: 99%

6-Alkyl-3,4-dihydro-2H-pyrans: Chemical Secretion Compounds in Neotropical Harvestmen

et al. 2011

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The defensive secretions of five neotropical species of harvestmen (Opiliones: Gonyleptidae) from the Brazilian Atlantic Forest were analyzed and chemically characterized by GC-MS and NMR methods. Three of the species, Cobania picea, Roweria virescens, and Serracutisoma proximum, secrete a mixture of 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3-methyl-1,4-benzoquinone. The secretions produced by the other two species, Iporangaia pustulosa and Neosadocus maximus, contain 1-hepten-3-one, 5-methyl-1-hexen-3-one, and 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone (1) as major components, as well as 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3-methyl-1,4-benzoquinone as minor constituents. The dihydropyran 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone (1) is a new natural product, composed of two 1-hepten-3-one subunits formally linked in a hetero-Diels-Alder reaction. The natural product was proven to be racemic, and its biogenetic origin is discussed.

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“…In contrast to ene-yne 16, the mixture of ene-ynes 18/19 was unreactive to either Grubbs' I or II catalyst (Scheme 5). This mixture was then oxidized with Jones reagent 16 Reduction of the terminal alkene of 22 went as expected and gave 24 was an inseparable 4:1 mixture of diastereomers. The ester group was then hydrolysed to the corresponding acid which was treated with CuBr 2 on alumina at 65 o C according to Mori's bromo-lactonization procedure.…”

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confidence: 86%

“…To a solution of alcohols 18/19 (50 mg, 0.16 mmol) in acetone (6 mL), was added Jones reagent 16 Ethyl 2-((1S,9aS)-1-(benzyloxy)-3-oxo-2,3,5,6,7,9a-1H-pyrrolo[1,2-a]azepin-9-yl) 1-(benzyloxy)-3-oxo-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a] (3aS,10S)-10-Hydroxy-1-methyl-3a,4,5,6,10,10a-hexahydro-2H-furo[3,2-c]pyrrolo[1,2-a]…”

Section: Ethyl 3-((4s5s)-4-(benzyloxy)-2-oxo-1-(pent-4-enyl)pyrrolidmentioning

confidence: 99%

Model Studies Towards the Total Synthesis of the Stemona Alkaloid 1-Hydroxyprotostemonine: Synthesis of ent-1-Hydroxystemoamide

Swamy¹,

Pyne²

2012

HETEROCYCLES

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Oxidative coupling of 2-substituted 1,2-dihydro-1-naphthols using Jones reagent: a simple entry into 3,3′-disubstituted 1,1′-binaphthyl-4,4′-diols

Cited by 9 publications

References 23 publications

Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

6-Alkyl-3,4-dihydro-2H-pyrans: Chemical Secretion Compounds in Neotropical Harvestmen

Model Studies Towards the Total Synthesis of the Stemona Alkaloid 1-Hydroxyprotostemonine: Synthesis of ent-1-Hydroxystemoamide

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