Enantiopure Aromatic Saddles Bearing the Fenestrindane Core

Wong W-S, Tse H-W, Cheung E, Kuck D, Chow H-F (2019)
JOURNAL OF ORGANIC CHEMISTRY 84(2): 869-878.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Wong, Wai-Shing; Tse, Ho-Wing; Cheung, Enoch; Kuck, DietmarUniBi; Chow, Hak-Fun
Abstract / Bemerkung
The synthesis of enantiomerically pure, configurationally stable fenestrindane-based polyaromatic compounds with saddle-like structures is reported. Seven racemic fenestrane synthetic precursors were first screened by chiral HPLC for resolvability into enantiomers. Among the three resolvable precursors, a tribenzofenestrene derivative was resolved on a semipreparative scale, and the absolute configuration of the more slowly eluting enantiomer was established by X-ray crystallography. The enantiopure tribenzofenestrenes were then separately converted, in six steps, to the saddle-shaped fenestrindane derivatives in optically pure form. The two enantiomeric pairs of saddles were characterized by H-1 and C-13 NMR spectroscopy, mass spectrometry, and circular dichroism spectroscopy. All new compounds reported herein represent the first enantiopure non-natural carbocyclic fenestranes isolated to date.
Erscheinungsjahr
2019
Zeitschriftentitel
JOURNAL OF ORGANIC CHEMISTRY
Band
84
Ausgabe
2
Seite(n)
869-878
ISSN
0022-3263
Page URI
https://pub.uni-bielefeld.de/record/2933915

Zitieren

Wong W-S, Tse H-W, Cheung E, Kuck D, Chow H-F. Enantiopure Aromatic Saddles Bearing the Fenestrindane Core. JOURNAL OF ORGANIC CHEMISTRY. 2019;84(2):869-878.
Wong, W. - S., Tse, H. - W., Cheung, E., Kuck, D., & Chow, H. - F. (2019). Enantiopure Aromatic Saddles Bearing the Fenestrindane Core. JOURNAL OF ORGANIC CHEMISTRY, 84(2), 869-878. doi:10.1021/acs.joc.8b02719
Wong, W. - S., Tse, H. - W., Cheung, E., Kuck, D., and Chow, H. - F. (2019). Enantiopure Aromatic Saddles Bearing the Fenestrindane Core. JOURNAL OF ORGANIC CHEMISTRY 84, 869-878.
Wong, W.-S., et al., 2019. Enantiopure Aromatic Saddles Bearing the Fenestrindane Core. JOURNAL OF ORGANIC CHEMISTRY, 84(2), p 869-878.
W.-S. Wong, et al., “Enantiopure Aromatic Saddles Bearing the Fenestrindane Core”, JOURNAL OF ORGANIC CHEMISTRY, vol. 84, 2019, pp. 869-878.
Wong, W.-S., Tse, H.-W., Cheung, E., Kuck, D., Chow, H.-F.: Enantiopure Aromatic Saddles Bearing the Fenestrindane Core. JOURNAL OF ORGANIC CHEMISTRY. 84, 869-878 (2019).
Wong, Wai-Shing, Tse, Ho-Wing, Cheung, Enoch, Kuck, Dietmar, and Chow, Hak-Fun. “Enantiopure Aromatic Saddles Bearing the Fenestrindane Core”. JOURNAL OF ORGANIC CHEMISTRY 84.2 (2019): 869-878.

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