Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes

Xu W-R, Chow H-F, Cao X-P, Kuck D (2014)
The Journal of Organic Chemistry 79(19): 9335-9346.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
The regiocontrolled syntheses of four chiral C-1- or C-3-symmetrical tribenzotriquinacene (TBTQ) derivatives bearing methoxy or hydroxy groups at the peripheral positions [(2,6-(OMe)(2), (+/-)-18 and (+/-)-20; 2,6-(OH)(2), (+/-)-19; and 2,6,10-(OMe)(3), (+/-)-21] by two different synthesis protocols are reported. Compounds (+/-)-19, (+/-)-20, and (+/-)-21 and two (already-known) monosubstituted C1-symmetrical TBTQ analogues [2-OH (+/-)-23 and 2-OMe (+/-)-24] were readily resolved by chiral HPLC, and their absolute configurations were determined by X-ray crystallography and/or circular dichroism (CD) studies. Optical resolution of three closely related TBTQ derivatives [2,6-(OMe)(2), (+/-)-18; 2-OMe, (+/-)-22; and 2-OH, (+/-)-25] containing the same peripheral substituents but other bridgehead residues failed. Enantiopure TBTQ derivatives of this sort are considered promising structural motifs toward the construction of molecular squares and cubes
Erscheinungsjahr
Zeitschriftentitel
The Journal of Organic Chemistry
Band
79
Zeitschriftennummer
19
Seite
9335-9346
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Xu W-R, Chow H-F, Cao X-P, Kuck D. Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry. 2014;79(19):9335-9346.
Xu, W. - R., Chow, H. - F., Cao, X. - P., & Kuck, D. (2014). Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry, 79(19), 9335-9346. doi:10.1021/jo501914y
Xu, W. - R., Chow, H. - F., Cao, X. - P., and Kuck, D. (2014). Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry 79, 9335-9346.
Xu, W.-R., et al., 2014. Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry, 79(19), p 9335-9346.
W.-R. Xu, et al., “Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes”, The Journal of Organic Chemistry, vol. 79, 2014, pp. 9335-9346.
Xu, W.-R., Chow, H.-F., Cao, X.-P., Kuck, D.: Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry. 79, 9335-9346 (2014).
Xu, Wen-Rong, Chow, Hak-Fun, Cao, Xiao-Ping, and Kuck, Dietmar. “Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes”. The Journal of Organic Chemistry 79.19 (2014): 9335-9346.

8 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Stereoselective synthesis of enantiomerically pure bowl-shaped hydroxytribenzotriquinacenes.
Rommelmann P, Nachtigall B, Guntelmann T, Gröger H, Kuck D., Org Biomol Chem 16(31), 2018
PMID: 30033471
Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration.
Kuck D, Linke J, Teichmann LC, Barth D, Tellenbröker J, Gestmann D, Neumann B, Stammler HG, Bögge H., Phys Chem Chem Phys 18(17), 2016
PMID: 26728545
Apical Functionalization of Tribenzotriquinacenes.
Dhara A, Weinmann J, Krause AM, Beuerle F., Chemistry 22(35), 2016
PMID: 27444414
Facile Assembly of Chiral Metallosquares by Using Enantiopure Tribenzotriquinacene Corner Motifs.
Xu WR, Xia GJ, Chow HF, Cao XP, Kuck D., Chemistry 21(34), 2015
PMID: 26126897
Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds.
Klotzbach S, Beuerle F., Angew Chem Int Ed Engl 54(35), 2015
PMID: 26136295
Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis.
Greschner W, Neumann B, Stammler HG, Gröger H, Kuck D., Angew Chem Int Ed Engl 54(46), 2015
PMID: 26404021

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