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

Research output: Journal article publicationJournal articleAcademic researchpeer-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

ASJC Scopus subject areas

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

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