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.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
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
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
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
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
Markopoulos G, Henneicke L, Shen J, Okamoto Y, Jones PG, Hopf H., Angew Chem Int Ed Engl 51(51), 2012
PMID: 23144000
Tribenzotriquinacenes bearing three peripheral or bridgehead urea groups stretched into the 3-D space.
Tellenbröker J, Kuck D., Beilstein J Org Chem 7(), 2011
PMID: 21512595
Tellenbröker J, Kuck D., Beilstein J Org Chem 7(), 2011
PMID: 21512595
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
Three-dimensional hydrocarbon cores based on multiply fused cyclopentane and indane units: centropolyindanes.
Kuck D., Chem. Rev. 106(12), 2006
PMID: 17165679
Kuck D., Chem. Rev. 106(12), 2006
PMID: 17165679
Kuck, Pure Appl. Chem. 78(), 2006
AUTHOR UNKNOWN, 0
Kuck, Top. Curr. Chem. 196(), 1998
Kuck, Liebigs Ann. (), 1997
Kuck, Synlett (), 1996
Nanosized ball joints constructed from C60 and tribenzotriquinacene sockets: synthesis, component self-assembly and structural investigations.
Bredenkotter B, Henne S, Volkmer D., Chemistry 13(35), 2007
PMID: 17907125
Bredenkotter B, Henne S, Volkmer D., Chemistry 13(35), 2007
PMID: 17907125
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
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
Langhals H, Rauscher M, Strube J, Kuck D., J. Org. Chem. 73(3), 2008
PMID: 18184004
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Solid-state enantiopure organic nanocubes formed by self organization of a C3-symmetrical tribenzotriquinacene.
Strube J, Neumann B, Stammler HG, Kuck D., Chemistry 15(10), 2009
PMID: 19191245
Strube J, Neumann B, Stammler HG, Kuck D., Chemistry 15(10), 2009
PMID: 19191245
Tellenbröker, Angew. Chem. 111(), 1999
Tribenzotriquinacenes with Sixfold Peripheral Functionalization-Potential Building Blocks for Novel Organic Networks.
Tellenbroker J, Kuck D., Angew. Chem. Int. Ed. Engl. 38(7), 1999
PMID: 29711878
Tellenbroker J, Kuck D., Angew. Chem. Int. Ed. Engl. 38(7), 1999
PMID: 29711878
C3v-symmetrical tribenzotriquinacenes extended by six C1-functional groups and the first triquinacene-based tris(dithiametacyclophanes).
Zhou L, Zhang TX, Li BR, Cao XP, Kuck D., J. Org. Chem. 72(17), 2007
PMID: 17658847
Zhou L, Zhang TX, Li BR, Cao XP, Kuck D., J. Org. Chem. 72(17), 2007
PMID: 17658847
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
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
MacGillivray LR, Atwood JL., Angew. Chem. Int. Ed. Engl. 38(8), 1999
PMID: 25138490
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
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
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
Synthesis and structure of a platinum(II) molecular square incorporating four fluxional thiacrown ligands: The crystal structure of [Pt4([9]aneS3)4(4,4'-bipy)4](OTf)8.
Janzen DE, Patel KN, VanDerveer DG, Grant GJ., Chem. Commun. (Camb.) (33), 2006
PMID: 16921438
Janzen DE, Patel KN, VanDerveer DG, Grant GJ., Chem. Commun. (Camb.) (33), 2006
PMID: 16921438
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
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
Chiral rodlike platinum complexes, double helical chains, and potential asymmetric hydrogenation ligand based on "linear" building blocks: 1,8,9,16-tetrahydroxytetraphenylene and 1,8,9,16-tetrakis(diphenylphosphino)tetraphenylene.
Peng HY, Lam CK, Mak TC, Cai Z, Ma WT, Li YX, Wong HN., J. Am. Chem. Soc. 127(26), 2005
PMID: 15984888
Peng HY, Lam CK, Mak TC, Cai Z, Ma WT, Li YX, Wong HN., J. Am. Chem. Soc. 127(26), 2005
PMID: 15984888
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
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
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
Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation.
Stephens PJ, Devlin FJ, Gasparrini F, Ciogli A, Spinelli D, Cosimelli B., J. Org. Chem. 72(13), 2007
PMID: 17516678
Stephens PJ, Devlin FJ, Gasparrini F, Ciogli A, Spinelli D, Cosimelli B., J. Org. Chem. 72(13), 2007
PMID: 17516678
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
Polavarapu PL, Jeirath N, Walia S., J Phys Chem A 113(18), 2009
PMID: 19366240
AUTHOR UNKNOWN, 0
Ball-, bowl-, and belt-shaped conjugated systems and their complexing abilities: exploration of the concave-convex pi-pi interaction.
Kawase T, Kurata H., Chem. Rev. 106(12), 2006
PMID: 17165687
Kawase T, Kurata H., Chem. Rev. 106(12), 2006
PMID: 17165687
Extreme conformational constraints in pi-extended tetrathiafulvalenes: unusual topologies and redox behavior of doubly and triply bridged cyclophanes.
Christensen CA, Batsanov AS, Bryce MR., J. Am. Chem. Soc. 128(32), 2006
PMID: 16895414
Christensen CA, Batsanov AS, Bryce MR., J. Am. Chem. Soc. 128(32), 2006
PMID: 16895414
AUTHOR UNKNOWN, 2004
Vögtle, 1993
Diederich, 1991
Seo, Tetrahedron Lett. 49(), 2008
AUTHOR UNKNOWN, 0
Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology.
Daniel MC, Astruc D., Chem. Rev. 104(1), 2004
PMID: 14719978
Daniel MC, Astruc D., Chem. Rev. 104(1), 2004
PMID: 14719978
Novel Cavity Design Using Calix[n]arene Skeletons: Toward Molecular Recognition and Metal Binding.
Ikeda A, Shinkai S., Chem. Rev. 97(5), 1997
PMID: 11851464
Ikeda A, Shinkai S., Chem. Rev. 97(5), 1997
PMID: 11851464
Cooperative recognition of a copper cation and anion by a calix[4]arene substituted at the lower rim by a beta-amino-alpha,beta-unsaturated ketone.
Senthilvelan A, Ho IT, Chang KC, Lee GH, Liu YH, Chung WS., Chemistry 15(25), 2009
PMID: 19449358
Senthilvelan A, Ho IT, Chang KC, Lee GH, Liu YH, Chung WS., Chemistry 15(25), 2009
PMID: 19449358
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 20853291
PubMed | Europe PMC
Suchen in
Google Scholar