Stereolabile chiral biphenyl hybrids: Crystallization-induced dynamic atropselective resolution involving supramolecular interactions

Chi Tung Yeung, Ho Lun Yeung, Wesley Ting Kwok Chan, Siu Cheong Yan, Eric C.Y. Tam, Ka-Leung WONG, Chi Sing LEE, Wing Tak Wong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)836-840
Number of pages5
JournalCrystEngComm
Volume15
Issue number5
DOIs
Publication statusPublished - 7 Feb 2013

Scopus Subject Areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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