http://dx.doi.org/10.1039/C2CE26438B">
 

Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

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

Language

English

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. © 2013 The Royal Society of Chemistry.

Publication Date

2013

Source Publication Title

CrystEngComm

Volume

15

Issue

5

Start Page

836

End Page

840

Publisher

Royal Society of Chemistry

ISSN (print)

14668033

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