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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 |
Issue Date: | 2019 | Source: | Molecules, 2019, v. 24, no. 3, 643 | 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. | Keywords: | Asymmetry Atropisomer Hydrogen bond N-nitroso aldol reaction |
Publisher: | Molecular Diversity Preservation International (MDPI) | Journal: | Molecules | 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 |
Appears in Collections: | Journal/Magazine Article |
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