Department of Chemistry
Stereolabile chiral biphenyl hybrids: crystallization-induced dynamic atropselective resolution involving supramolecular interactions
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. © 2013 The Royal Society of Chemistry.
Source Publication Title
Royal Society of Chemistry
Link to Publisher's Edition
Yeung, C., Yeung, H., Chan, W., Yan, S., Tam, E., Wong, K., Lee, C., & Wong, W. (2013). Stereolabile chiral biphenyl hybrids: crystallization-induced dynamic atropselective resolution involving supramolecular interactions. CrystEngComm, 15 (5), 836-840. https://doi.org/10.1039/C2CE26438B