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Issue 5, 2013
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Stereolabile chiral biphenyl hybrids: crystallization-induced dynamic atropselective resolution involving supramolecular interactions

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Abstract

Crystallization-induced dynamic atropselective resolutions of three simple chiral biphenyl hybrids, (1R,1′R)-1,1′-(biphenyl-2,2′-diyl)diethanol 1, (1R,1′R)-1,1′-(biphenyl-2,2′-diyl)bis(ethane-1,1-diyl)diacetate 2 and (1S,1′S)-1,1′-(biphenyl-2,2′-diyl)bis(2,2′-dimethylpropan-1-ol) 3 were achieved. The axial chirality of the biphenyl backbones of 1–3 were found to be determined by (i) the steric bulkiness at the α position of the ortho-substituents, and (ii) the intermolecular interactions between the molecules. 1, which possesses the least sterically demanding methyl substituents, was found to form stereoselectively the S-atropisomer and gave enantiomerically pure supramolecular right-handed helices through strong and directional intermolecular hydrogen bonds in its crystal.

Graphical abstract: Stereolabile chiral biphenyl hybrids: crystallization-induced dynamic atropselective resolution involving supramolecular interactions

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Publication details

The article was received on 05 Sep 2012, accepted on 13 Nov 2012 and first published on 15 Nov 2012


Article type: Communication
DOI: 10.1039/C2CE26438B
Citation: CrystEngComm, 2013,15, 836-840
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    Stereolabile chiral biphenyl hybrids: crystallization-induced dynamic atropselective resolution involving supramolecular interactions

    C. Yeung, H. Yeung, W. T. K. Chan, S. Yan, E. C. Y. Tam, K. Wong, C. Lee and W. Wong, CrystEngComm, 2013, 15, 836
    DOI: 10.1039/C2CE26438B

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