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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Abstract
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
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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.
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.
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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

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PMID: 25222797
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