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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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Article information


Submitted
05 Sep 2012
Accepted
13 Nov 2012
First published
15 Nov 2012

CrystEngComm, 2013,15, 836-840
Article type
Communication

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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