Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/80658
Title: Synthesis of a conformationally stable atropisomeric pair of biphenyl scaffold containing additional stereogenic centers
Authors: Yeung, CT 
Chan, WTK 
Lo, WS 
Law, GL 
Wong, WT 
Keywords: Asymmetry
Atropisomer
Hydrogen bond
N-nitroso aldol reaction
Issue Date: 2019
Publisher: Molecular Diversity Preservation International (MDPI)
Source: Molecules, 2019, v. 24, no. 3, 643 How to cite?
Journal: Molecules 
Abstract: The synthesis of a new CF 3 -containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF 3 and CH 3 groups very different. The synthesized stereogenic scaffold proved to be effective in catalyzing the asymmetric N-nitroso aldol reaction of enamine and nitrosobenzene. Compared to similar scaffolds without CF 3 groups, one of our atropisomer exhibits an increase in enantioselectivity in this reaction.
URI: http://hdl.handle.net/10397/80658
ISSN: 1420-3049
DOI: 10.3390/molecules24030643
Rights: © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
The following publication Yeung, C. T., Chan, W. T. K., Lo, W. S., Law, G. L., & Wong, W. T. (2019). Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers. Molecules, 24(3), 643 is available at https://doi.org/10.3390/molecules24030643
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