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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
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.
ISSN: 1420-3049
DOI: 10.3390/molecules24030643
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