Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution

Li Z-M, Tan Y, Ma Y-P, Cao X-P, Chow H-F, Kuck D (2020)
JOURNAL OF ORGANIC CHEMISTRY 85(10): 6478-6488.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Autor*in
Li, Zhi-Min; Tan, Yingfei; Ma, You-Ping; Cao, Xiao-Ping; Chow, Hak-Fun; Kuck, DietmarUniBi
Abstract / Bemerkung
Starting from a hitherto unknown 2-aminotribenzo-triquinacene, several 2-amino-3-X-substituted TBTQ derivatives, all bearing a single ortho-difunctionalized indane wing, were synthesized as rigid and chiral building blocks for the potential construction of complex supramolecular architectures. Efficient access to two pairs of enantiomeric TBTQ derivatives, namely, the peripheral ortho-nitroaniline (X = NO2) and the related anthranilic acid (X = CO2H), was developed using chiral auxiliaries as the resolving reagents. The structure of the intermediate diastereomers was confirmed by H-1 and C-13 NMR spectroscopy, high-resolution mass spectroscopy (HRMS), and polarimetry. The absolute configuration of the optically active derivatives was confirmed by quantum chemical time-dependent density functional theory (TD-DFT) calculations of the theoretical electronic circular dichroism (ECD) spectra and by single-crystal X-ray structure analysis of a synthesis intermediate.
Erscheinungsjahr
2020
Zeitschriftentitel
JOURNAL OF ORGANIC CHEMISTRY
Band
85
Ausgabe
10
Seite(n)
6478-6488
ISSN
0022-3263
eISSN
1520-6904
Page URI
https://pub.uni-bielefeld.de/record/2943806

Zitieren

Li Z-M, Tan Y, Ma Y-P, Cao X-P, Chow H-F, Kuck D. Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution. JOURNAL OF ORGANIC CHEMISTRY. 2020;85(10):6478-6488.
Li, Z. - M., Tan, Y., Ma, Y. - P., Cao, X. - P., Chow, H. - F., & Kuck, D. (2020). Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution. JOURNAL OF ORGANIC CHEMISTRY, 85(10), 6478-6488. doi:10.1021/acs.joc.0c00396
Li, Z. - M., Tan, Y., Ma, Y. - P., Cao, X. - P., Chow, H. - F., and Kuck, D. (2020). Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution. JOURNAL OF ORGANIC CHEMISTRY 85, 6478-6488.
Li, Z.-M., et al., 2020. Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution. JOURNAL OF ORGANIC CHEMISTRY, 85(10), p 6478-6488.
Z.-M. Li, et al., “Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution”, JOURNAL OF ORGANIC CHEMISTRY, vol. 85, 2020, pp. 6478-6488.
Li, Z.-M., Tan, Y., Ma, Y.-P., Cao, X.-P., Chow, H.-F., Kuck, D.: Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution. JOURNAL OF ORGANIC CHEMISTRY. 85, 6478-6488 (2020).
Li, Zhi-Min, Tan, Yingfei, Ma, You-Ping, Cao, Xiao-Ping, Chow, Hak-Fun, and Kuck, Dietmar. “Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution”. JOURNAL OF ORGANIC CHEMISTRY 85.10 (2020): 6478-6488.

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 32271016
PubMed | Europe PMC

Suchen in

Google Scholar