Structural studies on the stereoisomerism of a natural dye miraxanthin I

2019 ◽  
Vol 43 (46) ◽  
pp. 18165-18174 ◽  
Author(s):  
Stanisław Niziński ◽  
Łukasz Popenda ◽  
Michał F. Rode ◽  
Agnieszka Kumorkiewicz ◽  
Zbigniew Fojud ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Bond Formation ◽  
Natural Dye ◽  
Torsional Motion ◽  
Structural Studies ◽  
Hydrogen Bond Formation ◽  
Intramolecular Hydrogen

Fluorescence in miraxanthin I is enhanced by intramolecular hydrogen bond formation hampering torsional motion around the central bonds.

scholarly journals Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 643 ◽  
Author(s):  
Chi-Tung Yeung ◽  
Wesley Chan ◽  
Wai-Sum Lo ◽  
Ga-Lai Law ◽  
Wing-Tak Wong
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Bond Formation ◽  
Aldol Reaction ◽  
Spatial Arrangement ◽  
Hydroxyl Groups ◽  
Hydrogen Bond Formation ◽  
X Ray ◽  
Stereogenic Centers ◽  
Intramolecular Hydrogen

The synthesis of a new CF3-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 CF3 and CH3 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 CF3 groups, one of our atropisomer exhibits an increase in enantioselectivity in this reaction.

Sign in / Sign up

Export Citation Format

Share Document