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, Chi-Tung, Ho-Lun Yeung, Wesley Ting Kwok Chan, Siu-Cheong Yan, Eric C. Y. Tam, Ka-Leung Wong, Chi-Sing Lee, and Wing-Tak Wong. "Stereolabile chiral biphenyl hybrids: crystallization-induced dynamic atropselective resolution involving supramolecular interactions." CrystEngComm 15.5 (2013): 836-840.