Stereoselective reactions of esters/amides and their surrogates catalyzed by bifunctional organocatalysts and enantioselective separation of secondary alcohols by hydrogenbonded organic framework

Guang, Jie
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Ester and amide are among the most common and important functionalities in the organic synthesis of bioactive molecules. However, due to the high pKa value of the alpha-proton in the ester and amide compounds, a general asymmetric catalytic methodology for the direct activation of ester or amide is still elusive. To obtain the desired products via asymmetric catalysis, various masked synthetic equivalents of ester/amide (surrogates) have been designed in the past decades. The first chapter of this dissertation describes my doctoral research on the organocatalyzed stereoselective reactions of esters/amides and their surrogates, namely, the organocatalyzed reactions of modified N -acyl oxazolidinones and thioesters for the enantioselective synthesis of cyclic thiocarbamates with a spirooxindole moiety and N -protected beta-amino thioesters, respectively; the novel application of acetylphosphonates as ester/amide surrogates in asymmetric catalysis, such as the organocatalyzed aldol reaction and Michael reaction; and the direct employment of unactivated esters in organocatalyzed carbon-carbon formation reactions. The second chapter of this dissertation describes my contribution to the enantioselective separation of secondary alcohols by using hydrogen-bonded organic frameworks, which provides an efficient and economic method for the resolution of racemic secondary alcohols.

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Asymmetric Catalysis, Bifunctional Organocatalyst, Ester Surrogate, Hydrogen-Bonded Organic Framework, Organocatalysis, Unmodified Carbonyl Compounds