Stereoselective Cyclotrimerization of Enantiopure Iodonorbornenes Catalyzed by Pd Nanoclusters for C3 or C3v Symmetric syn-Tris(norborneno)benzenes

Higashibayashi, Shuhei; Abdollahi, Reza; Sakurai, Hidehiro

doi:10.1021/jo100710h

Cited by 33 publications

(15 citation statements)

References 35 publications

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“…2. Enantiopure (1S, 4R)-2 was converted to syn-3 exclusively under Pd-catalysed cyclotrimerization conditions 27 . Compound 3 was hydrolysed, followed by condensation, to afford the non-conjugated bowl-shaped lactam 4.…”

Section: Synthesis Of Triazasumanenesmentioning

confidence: 99%

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Enantioselective synthesis of a chiral nitrogen-doped buckybowl

et al. 2012

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Bowl-shaped aromatic compounds, namely buckybowls constitute a family of curved polycyclic aromatic carbons along with fullerenes and carbon nanotubes. Doping of heteroatoms to the carbon frameworks of such aromatic compounds drastically modulates their physical and chemical properties. In contrast to nitrogen-doped azafullerenes or carbon nanotubes, synthesis of azabuckybowls, nitrogen-doped buckybowls, remains an unsolved challenging task. Here we report the first enantioselective synthesis of a chiral azabuckybowl, triazasumanene. X-ray crystallographic analysis confirmed that the doping of nitrogen induces a more curved and deeper bowl structure than in all-carbon buckybowls. As a result of the deeper bowl structure, the activation energy for the bowl inversion (thermal flipping of the bowl structure) reaches an extraordinarily high value (42.2 kcal per mol). As the bowl inversion corresponds to the racemization process for chiral buckybowls, this high bowl inversion energy leads to very stable chirality of triazasumanene.

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Section: Synthesis Of Triazasumanenesmentioning

confidence: 99%

“…Other reagents were used as received without further purification. Both enantiomers of compound 2 and compound 3 were prepared according to our reported method 27 Ar atmosphere. The mixture was stirred at 25 °C for 8 h, during which the colour changed from yellow to dark red.…”

Section: Materials and Characterizationmentioning

confidence: 99%

Enantioselective synthesis of a chiral nitrogen-doped buckybowl

et al. 2012

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“…As in the synthesis of sumanene, Pd-catalyzed syn-selective cyclotrimerization yielded syn-tris(norborneno)benzene 126 [146][147][148]. This newly developed protocol is more efficient than the conventional method reported in Scheme 36.…”

Section: Scheme 35mentioning

confidence: 93%

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Siegel

2014

Polyarenes I

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This chapter summarizes the synthesis, physical properties, structure, and crystal packing of buckybowls. Buckybowls exemplify an intermediate class of polynuclear aromatic compounds between the closed-shell fullerenes and the flat extended arrays of graphene. These warped sheets can be seen as fragments of fullerenes or the end cap of single-walled carbon nanotubes; and, their curvature endows them with physical properties distinct from flat polynuclear hydrocarbons, which opens up unique possibilities for molecular bowls in various organic materials applications.

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“…Therefore, economical and environmental oxidants have been developed. To date, numerous transition-metalcatalyzed aerobic oxidations of alcohols have been developed, such as palladium [15,16], gold [17] and ruthenium [18]. Besides, Uyanik [19] found that the catalytic system consisting of HBr/NaNO 2 was effective for the aerobic oxidation of alcohols.…”

Section: Introductionmentioning

confidence: 99%

Improved synthesis of 2-norbornanone

Zhang

Tao

et al. 2015

Res Chem Intermed

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Herein a two-step process for the synthesis of 2-norbornanone with 91 % overall yield has been developed. The addition of sublimation inhibitors suppressed the sublimation of norbornene in the process of sulfuric acid-promoted hydration and increased the yield of 2-norbornanol significantly under mild conditions. Additionally, reuse of sulfuric acid has been achieved. A 4-hydroxy-TEMPO/CuCl/TBN triplecomponent catalyst system for the highly selective aerobic oxidation of 2-norbornanol was developed and displayed high atom efficiency and yield.

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Stereoselective Cyclotrimerization of Enantiopure Iodonorbornenes Catalyzed by Pd Nanoclusters for C₃ or C_3v Symmetric syn-Tris(norborneno)benzenes

Cited by 33 publications

References 35 publications

Enantioselective synthesis of a chiral nitrogen-doped buckybowl

Enantioselective synthesis of a chiral nitrogen-doped buckybowl

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Improved synthesis of 2-norbornanone

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