Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers

Wang T, Hou Q-Q, Teng Q-F, Yao X-J, Niu W-X, Cao X-P, Kuck D (2010)
CHEMISTRY-A EUROPEAN JOURNAL 16(41): 12412-12424.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Wang, Tao; Hou, Qin-Qing; Teng, Qing-Feng; Yao, Xiao-Jun; Niu, Wen-Xue; Cao, Xiao-Ping; Kuck, DietmarUniBi
Abstract / Bemerkung
Enantiomerically pure tribenzotriquinacenes (TBTQs) bearing two monofunctionalized aromatic nuclei were synthesized for the first time and their optical properties and absolute configuration determined. A remarkably regioselective bis-formylation of the fully bridgehead methylated parent TBTQ hydrocarbon with MeOCHCl2/TiCl4 afforded a mixture of two C-s-symmetrical (achiral) difunctionalized derivatives together with one C-1-symmetrical (chiral) isomer. Reduction and subsequent column chromatography furnished the three respective benzylic TBTQ dialcohols. Optical resolution of the racemic 2,6-bis(hydroxymethyl) derivative was achieved via the diastereomeric (R)-1,1'-bi-2-naphthol ethers and the absolute configuration of the enantiomers was determined by CD exciton model analysis. The electronic circular dichroism (ECD) spectra and the specific rotation of the enantiomers were found to agree with the results of DFT calculations. Among the C-s-symmetrical isomers, the "proximal" 2,11-dialdehyde and the corresponding benzylic dialcohol were identified by 2D NMR spectroscopy and X-ray crystallographic analysis, respectively, and used as the starting point for the synthesis of several novel dithiametacyclophanes. These include the first "dimeric" tribenzotriquinacene-based cyclophanes bearing the bowls of the two TBTQ units attached to each other in a syn (concave-concave) or anti (convex-concave) configuration. The usefulness of such thiacyclophanes as fluorescent chemosensors for different metal ions is also demonstrated.
Stichworte
formylation; configuration determination; regioselectivity; synthetic; methods; tribenzotriquinacenes
Erscheinungsjahr
2010
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
16
Ausgabe
41
Seite(n)
12412-12424
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/1929210

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Wang T, Hou Q-Q, Teng Q-F, et al. Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers. CHEMISTRY-A EUROPEAN JOURNAL. 2010;16(41):12412-12424.
Wang, T., Hou, Q. - Q., Teng, Q. - F., Yao, X. - J., Niu, W. - X., Cao, X. - P., & Kuck, D. (2010). Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers. CHEMISTRY-A EUROPEAN JOURNAL, 16(41), 12412-12424. doi:10.1002/chem.201001620
Wang, T., Hou, Q. - Q., Teng, Q. - F., Yao, X. - J., Niu, W. - X., Cao, X. - P., and Kuck, D. (2010). Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers. CHEMISTRY-A EUROPEAN JOURNAL 16, 12412-12424.
Wang, T., et al., 2010. Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers. CHEMISTRY-A EUROPEAN JOURNAL, 16(41), p 12412-12424.
T. Wang, et al., “Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 16, 2010, pp. 12412-12424.
Wang, T., Hou, Q.-Q., Teng, Q.-F., Yao, X.-J., Niu, W.-X., Cao, X.-P., Kuck, D.: Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers. CHEMISTRY-A EUROPEAN JOURNAL. 16, 12412-12424 (2010).
Wang, Tao, Hou, Qin-Qing, Teng, Qing-Feng, Yao, Xiao-Jun, Niu, Wen-Xue, Cao, Xiao-Ping, and Kuck, Dietmar. “Tribenzotriquinacenes Based on Regioselective Bis-formylation: Optical Resolution and Absolute Configuration of Inherently Chiral Derivatives and Synthesis of the First Cyclophane-Type Tribenzotriquinacene Dimers”. CHEMISTRY-A EUROPEAN JOURNAL 16.41 (2010): 12412-12424.

5 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
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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Brandenburg JG, Grimme S, Jones PG, Markopoulos G, Hopf H, Cyranski MK, Kuck D., Chemistry 19(30), 2013
PMID: 23766137
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Markopoulos G, Henneicke L, Shen J, Okamoto Y, Jones PG, Hopf H., Angew Chem Int Ed Engl 51(51), 2012
PMID: 23144000

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