Tribenzotriquinacene: A Versatile Synthesis and <i>C</i><sub>3</sub>‐Chiral Platforms

Μαρκόπουλος, Γεώργιος; Henneicke, Lars; Shen, Jun; Jones, Peter G.; Hopf, Henning

doi:10.1002/anie.201207220

Cited by 60 publications

(54 citation statements)

References 51 publications

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“…(1,T BTQ,F igure 1) [1][2][3] provides au nique and highly interesting combination of structural and chemical properties: Structurally,t he mutual fusion of the three indane wings generates a C 3v -symmetrical and conformationally rigid scaffold, the three wings point into the three-dimensional space at almost right angles,and the TBTQ bowl adopts apronounced concavity. [4][5][6][7] Chemically,t he four bridgehead positions and the six outer positions of the aromatic periphery can be functionalized independently and in various ways and the electronic interaction of the three benzene units is negligible.…”

Section: Thepolycyclicmolecularframeworkoftribenzotriquinacenementioning

confidence: 99%

Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis

et al. 2015

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Inherently chiral acetophenones and benzaldehydes bearing the large, bowl-shaped framework of tribenzotriquinacene (TBTQ) were synthesized in enantiomerically pure form employing enzyme catalysis. Five-step sequences involving lipase CAL-B lead to the (M)-enantiomers, (+)-2-acetyl-TBTQ (M)-5 and (+)-2-formyl-TBTQ (M)-6, whereas use of lipase PS leads to the (P)-enantiomers, (-)-2-acetyl-TBTQ (P)-5 and (-)-2-formyl-TBTQ (P)-6, with at least 99% ee in each case. The absolute configuration of these rigid 3D building blocks was determined by X-ray diffraction analysis of the ketones 5 and by comparison of their chiroptical properties with those of the aldehydes 6.

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Section: Thepolycyclicmolecularframeworkoftribenzotriquinacenementioning

confidence: 99%

Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis

et al. 2015

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“…The bowl-shaped polycyclic structure of tribenzotriquinacene [1][2][3] (TBTQ; 1, Figure 1) is an inspiring all-carbon motif that has motivated a number of researchers [4][5][6][7][8][9][10][11][12][13][14][15] since the publication of the first congener, the 12d-methyl-substituted derivative, in 1984. [16] One of the fascinating features of the conformationally rigid, C 3v -symmetrical TBTQ framework [17,18] is the suitability of the three three-dimensional bays for bridging by C 2 -units, such as 1,2-vinylidene and 1,2-phenylene groups (e.g.…”

Section: Introductionmentioning

confidence: 99%

Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl‐Shaped Core

et al. 2014

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The synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl-shaped molecular scaffold has been achieved by use of different strategies. Although the C 1 -and C 3 -symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding C 1 -and C 3 -symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained

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“…[1] First, these molecules may exhibit intrinsic chirality, [2] which may potentially lead to the formation of non-centrosymmetric stacks in which helical chirality evolves from the molecule itself [3] and not from chiral centers present in peripheral side chains. [1] First, these molecules may exhibit intrinsic chirality, [2] which may potentially lead to the formation of non-centrosymmetric stacks in which helical chirality evolves from the molecule itself [3] and not from chiral centers present in peripheral side chains.…”

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confidence: 99%