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Issue 26, 2015
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Diastereoselective cyclization of an aminobenzoic acid derivative and chiroptical properties of triple-stranded helical bis(phenylethynyl)benzene

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Abstract

The diastereoselective cyclization of 2,5-dibromo-4-hexylaminobenzoic acid was achieved by the microwave-assisted condensation using SiCl4. Moreover, the triple-stranded helical structure of bis(phenylethynyl)benzene units embedded in the cyclic tri(benzamide) scaffold was obtained by a Sonogashira–Hagihara coupling reaction. Two optically active enantiomers that do not racemize even at the elevated temperature were separated by chiral HPLC. The chiral helical topology was revealed by the spectroscopic data and theoretical calculation.

Graphical abstract: Diastereoselective cyclization of an aminobenzoic acid derivative and chiroptical properties of triple-stranded helical bis(phenylethynyl)benzene

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Publication details

The article was received on 02 Feb 2015, accepted on 17 Feb 2015 and first published on 18 Feb 2015


Article type: Communication
DOI: 10.1039/C5CC00945F
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2015,51, 5710-5713
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    Diastereoselective cyclization of an aminobenzoic acid derivative and chiroptical properties of triple-stranded helical bis(phenylethynyl)benzene

    R. Yamakado, S. Matsuoka, M. Suzuki, D. Takeuchi, H. Masu, I. Azumaya and K. Takagi, Chem. Commun., 2015, 51, 5710
    DOI: 10.1039/C5CC00945F

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