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Preparation of chiral amides and their use as organocatalysts
Brandejsová, Aneta ; Veselý, Jan (advisor) ; Hrdina, Radim (referee)
This bachelor thesis is focused on preparation of C-9 amino derivatives of Cinchona alkaloids and derived bifunctional squaramide catalysts, which are used as organocatalysts in a wide variety of chemical transformations leading to enantiomerically pure compounds. The first part deals with choosing the most efficient method for the preparation of C-9 amino derivates of Cinchona alkaloids and the synthesis of four selected examples. In the second part, the prepared derivates are used for the synthesis of bifunctional squaramide catalysts, which are further tested in newly designed cyclization reactions.
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Synthesis of cyclodextrin derivatives for organocatalysis
Chena Tichá, Iveta
Synthesis of cyclodextrin derivatives for organocatalysis This doctoral thesis examines the preparation of new cyclodextrin (CD) derivatives suitable for organocatalysis. The aim of this work is to prepare monosubstituted and disubstituted CD derivatives as organocatalysts for different types of enantioselective reactions potentially performed in water. In addition, disubstituted CD derivatives require considering the potential mixture of regioisomers and pseudoenantiomers. Thus, this thesis is divided into several sections - preparation of CD precursors and derivatives for organocatalysis, preparation of pure regioisomers and pseudoenantiomers of disubstituted CDs and final application of CD derivatives in enantioselective reactions. Furthermore, this thesis also focuses on the molecular modeling of the prepared CD derivatives and on their catalytic activity in silico. The first section covers the preparation of new disubstituted CD precursors as pure regioisomers for organocatalysts, specifically to develop a new method for the preparation of heterodisubstituted AC regioisomers on the primary rim of α-CD. This section also includes the determination of the regioisomer ratios of common α-CD intermediates disubstituted on the primary rim to evaluate their potential as precursors in organocatalysis....
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Synthesis of cyclodextrin derivatives for organocatalysis
Chena Tichá, Iveta
Synthesis of cyclodextrin derivatives for organocatalysis This doctoral thesis examines the preparation of new cyclodextrin (CD) derivatives suitable for organocatalysis. The aim of this work is to prepare monosubstituted and disubstituted CD derivatives as organocatalysts for different types of enantioselective reactions potentially performed in water. In addition, disubstituted CD derivatives require considering the potential mixture of regioisomers and pseudoenantiomers. Thus, this thesis is divided into several sections - preparation of CD precursors and derivatives for organocatalysis, preparation of pure regioisomers and pseudoenantiomers of disubstituted CDs and final application of CD derivatives in enantioselective reactions. Furthermore, this thesis also focuses on the molecular modeling of the prepared CD derivatives and on their catalytic activity in silico. The first section covers the preparation of new disubstituted CD precursors as pure regioisomers for organocatalysts, specifically to develop a new method for the preparation of heterodisubstituted AC regioisomers on the primary rim of α-CD. This section also includes the determination of the regioisomer ratios of common α-CD intermediates disubstituted on the primary rim to evaluate their potential as precursors in organocatalysis....
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Synthesis of cyclodextrin derivatives for organocatalysis
Chena Tichá, Iveta ; Jindřich, Jindřich (advisor) ; Lhoták, Pavel (referee) ; Šindelář, Vladimír (referee)
Synthesis of cyclodextrin derivatives for organocatalysis This doctoral thesis examines the preparation of new cyclodextrin (CD) derivatives suitable for organocatalysis. The aim of this work is to prepare monosubstituted and disubstituted CD derivatives as organocatalysts for different types of enantioselective reactions potentially performed in water. In addition, disubstituted CD derivatives require considering the potential mixture of regioisomers and pseudoenantiomers. Thus, this thesis is divided into several sections - preparation of CD precursors and derivatives for organocatalysis, preparation of pure regioisomers and pseudoenantiomers of disubstituted CDs and final application of CD derivatives in enantioselective reactions. Furthermore, this thesis also focuses on the molecular modeling of the prepared CD derivatives and on their catalytic activity in silico. The first section covers the preparation of new disubstituted CD precursors as pure regioisomers for organocatalysts, specifically to develop a new method for the preparation of heterodisubstituted AC regioisomers on the primary rim of α-CD. This section also includes the determination of the regioisomer ratios of common α-CD intermediates disubstituted on the primary rim to evaluate their potential as precursors in organocatalysis....
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