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Synthesis of Some Novel Chiral Dendrimers 1,1-Binaphthyl Derivatives
[Thesis]. Manchester, UK: The University of Manchester; 2011.
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Abstract
Despite a number of reports on synthetic methods for 1,1'- binaphthyl molecules with a substitution in certain positions, to the best of our knowledge neither the synthesis of binaphthyl-based chiral dendrimers by 1,3-cycloaddition reactions, "Click" chemistry, or attempts to achieve the substitution in multiple potential positions on binaphthyl cores has been studied yet. Previously reported optically active binaphthyl-based dendrimers have shown application in a number of applications, such as in asymmetric catalysts, enantioselective fluorescent sensors and chiral molecular recognition. Therefore, this project will focus on the synthesis of some novel chiral multiply functionalized 1,1'-binaphthyl molecules, including those that contain suitable groups to enable "Click" reactions and to facilitate the synthesis of some symmetric and asymmetric chiral dendrimers.
Layman's Abstract
Summary of route for synthesis of chiral bionapthol core:The project work started from rac-2,2-dihydroxy-1,1-binaphthyl and required the complete resolution into its optically pure (R) and (S)-enantiomers by the use of a chiral resolving agent. The isolated (R)-enantiomer was then reacted with proporgyl bromide . The resulting mono-propargyl system was then dimerized with 1,3-bis(bromomethyl)benzene or 1,6-dibromohexane as the connector between two (R)-enantiomeric binaphtols. Finally, attempts were undertaken to synthesise 1,3-bis((R)-2-methoxy-2’-propagyloxy-1,1’-binaphthly) benzene R-5 and 1,3-bis((R)-2-oxo-2’-propagyloxy-1,1’-binaphthly)hexane R-6 with 2nd generation Fréchet-type dendron 5.