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
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
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

Zitieren

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. https://doi.org/10.1002/chem.201001620
Wang, Tao, Hou, Qin-Qing, Teng, Qing-Feng, Yao, Xiao-Jun, Niu, Wen-Xue, Cao, Xiao-Ping, and Kuck, Dietmar. 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.
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
Unidirectional molecular stacking of tribenzotriquinacenes in the solid state: a combined X-ray and theoretical study.
Brandenburg JG, Grimme S, Jones PG, Markopoulos G, Hopf H, Cyranski MK, Kuck D., Chemistry 19(30), 2013
PMID: 23766137
Tribenzotriquinacene: a versatile synthesis and C3-chiral platforms.
Markopoulos G, Henneicke L, Shen J, Okamoto Y, Jones PG, Hopf H., Angew Chem Int Ed Engl 51(51), 2012
PMID: 23144000

86 References

Daten bereitgestellt von Europe PubMed Central.


Kuck, Angew. Chem. 96(), 1984

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 23(), 1984

Kuck, Angew. Chem. 101(), 1989

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 28(), 1989

Kuck, Chem. Ber. 125(), 1992

Kuck, Chem. Ber. 127(), 1994

Haag, J. Am. Chem. Soc. 117(), 1995

Kuck, Tetrahedron 57(), 2001

AUTHOR UNKNOWN, 0

Woodward, J. Am. Chem. Soc. 86(), 1964

Jacobson, Acta Chem. Scand. 21(), 1967

de, Angew. Chem. 83(), 1971

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 10(), 1971

Deslongchamps, Can. J. Chem. 56(), 1978

Gupta, J. Am. Chem. Soc. 111(), 1989

AUTHOR UNKNOWN, 0

Kuck, Pure Appl. Chem. 78(), 2006

AUTHOR UNKNOWN, 0

Kuck, Top. Curr. Chem. 196(), 1998

Kuck, Liebigs Ann. (), 1997

Kuck, Synlett (), 1996
C3v-symmetrical tribenzotriquinacenes as hosts for C60 and C70 in solution and in the solid state.
Georghiou PE, Dawe LN, Tran HA, Strube J, Neumann B, Stammler HG, Kuck D., J. Org. Chem. 73(22), 2008
PMID: 18850747
Three orthogonal chromophores operating independently within the same molecule.
Langhals H, Rauscher M, Strube J, Kuck D., J. Org. Chem. 73(3), 2008
PMID: 18184004

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Tellenbröker, Angew. Chem. 111(), 1999

Schuster, Angew. Chem. 103(), 1991

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 30(), 1991

Zhang, J. Org. Chem. 27(), 2007

AUTHOR UNKNOWN, 0

Gutsche, 1998

AUTHOR UNKNOWN, 2001

AUTHOR UNKNOWN, 0

Collet, Tetrahedron 43(), 1987

Collet, Top. Curr. Chem. 165(), 1993

Schmuck, Synthesis (), 2002
Cryptophanes and their complexes--present and future.
Brotin T, Dutasta JP., Chem. Rev. 109(1), 2009
PMID: 19086781

AUTHOR UNKNOWN, 0

Cram, Nature 356(), 1992

MacGillivray, Angew. Chem. 111(), 1999
Structural classification and general principles for the design of spherical molecular hosts.
MacGillivray LR, Atwood JL., Angew. Chem. Int. Ed. Engl. 38(8), 1999
PMID: 25138490
Carceplexes and Hemicarceplexes.
Jasat A, Sherman JC., Chem. Rev. 99(4), 1999
PMID: 11848996

Moors, Angew. Chem. 106(), 1994

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 33(), 1994
Convergent dendrons and dendrimers: from synthesis to applications.
Grayson SM, Frechet JM., Chem. Rev. 101(12), 2001
PMID: 11740922

AUTHOR UNKNOWN, 0
Redox non-innocence of thioether macrocycles: elucidation of the electronic structures of mononuclear complexes of gold(II) and silver(II).
Shaw JL, Wolowska J, Collison D, Howard JA, McInnes EJ, McMaster J, Blake AJ, Wilson C, Schroder M., J. Am. Chem. Soc. 128(42), 2006
PMID: 17044711

Vetrichelvan, Dalton Trans. (), 2003

AUTHOR UNKNOWN, 0

Poriel, Synth. Met. 158(), 2008

Mattiello, Synth. Commun. 31(), 2001
Curve-structured phenalenyl chemistry: synthesis, electronic structure, and bowl-inversion barrier of a phenalenyl-fused corannulene anion.
Nishida S, Morita Y, Ueda A, Kobayashi T, Fukui K, Ogasawara K, Sato K, Takui T, Nakasuji K., J. Am. Chem. Soc. 130(45), 2008
PMID: 18937470

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Lin, 2001

Dalla, New J. Chem. 28(), 2004

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
Preparation of both antipodes of enantiopure inherently chiral calix[4]crowns.
Cao YD, Luo J, Zheng QY, Chen CF, Wang MX, Huang ZT., J. Org. Chem. 69(1), 2004
PMID: 14703401

AUTHOR UNKNOWN, 0

Haratr, 1983

Hör, J. Org. Chem. 63(), 1998

Superchi, Org. Lett. 1(), 1999
Derivatization, complexation, and absolute configurational assignment of chiral primary amines: application of exciton-coupled circular dichroism.
Zhang J, Holmes AE, Sharma A, Brooks NR, Rarig RS, Zubieta J, Canary JW., Chirality 15(2), 2003
PMID: 12520510

AUTHOR UNKNOWN, 0

Diedrich, J. Phys. Chem. A 107(), 2003
Conformational sensitivity of chiroptical spectroscopic methods: 6,6'-dibromo-1,1'-bi-2-naphthol.
Polavarapu PL, Jeirath N, Walia S., J Phys Chem A 113(18), 2009
PMID: 19366240

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 2004

Vögtle, 1993

Diederich, 1991

Seo, Tetrahedron Lett. 49(), 2008

AUTHOR UNKNOWN, 0
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 20853291
PubMed | Europe PMC

Suchen in

Google Scholar