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Organocatalytic asymmetric synthesis of various organic compounds from α,β-unsaturated aledyhes
Kamlar, Martin ; Veselý, Jan (advisor) ; Trnka, Tomáš (referee)
With regard to a fast development in the field of fluoroorganic chemisty, the intention of this diploma thesis is focused to utilize of organocatalysis by secondary amines as catalysts for preparation enantiomerically pure compounds containing fluorine atom in its structure. The preparation of these subsances is realized by way of nucleofilic addition to α,β- unsaturated aldehydes using suitable fluorine containing nuclephilic agent 1-(fluoronitromethylsulphonyl)benzene, to get appropriate 1,4-adduct.
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Enantioselective allylation of thiophene-2-carbaldehyde
Motloch, Petr ; Kotora, Martin (advisor) ; Veselý, Jan (referee)
The first part of the bachelor thesis deals with enantioselective allylation of thiophene-2- carbaldehyde to the corresponding chiral homoallylic alcohol by using chiral Lewis bases as catalysts. The highest asymmetric induction achieved was 97 % ee. The second part concerns application of the prepared chiral homoallylic alcohol as the crucial intermediate for synthesis of antidepressant (S)-duloxetine. Key words enantioselective, allylation, Lewis base, thiophene-2-carbaldehyde, duloxetine
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Enantioselective synthesis of fluorinated organic compounds using iminium and enamine catalysis
Hejnová, Monika ; Veselý, Jan (advisor) ; Smrček, Stanislav (referee)
This diploma thesis deals with the scope of organocatalytic concept for the preparation of enantiomerically pure organic compounds, containing fluorine atom. Our attention was focused on the use of easily available α,β-unsaturated aldehydes and ketones as starting materials and commercially available secondary amines as catalysts. The first part of the work is dedicated to the enantioselective cyclization reaction of hydrazone (24) with cyclohex-2-enone (25). The second part describes a study of enantioselective nucleophilic addition of diethyl 2-fluoromalonate (31a) to α,β-unsaturated aldehydes (30) via enamine activation.
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Enantioselective allylation of thiophene-2-carbaldehyde
Motloch, Petr ; Kotora, Martin (advisor) ; Veselý, Jan (referee)
The first part of the bachelor thesis deals with enantioselective allylation of thiophene-2- carbaldehyde to the corresponding chiral homoallylic alcohol by using chiral Lewis bases as catalysts. The highest asymmetric induction achieved was 97 % ee. The second part concerns application of the prepared chiral homoallylic alcohol as the crucial intermediate for synthesis of antidepressant (S)-duloxetine. Key words enantioselective, allylation, Lewis base, thiophene-2-carbaldehyde, duloxetine
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Organocatalytic asymmetric synthesis of various organic compounds from α,β-unsaturated aledyhes
Kamlar, Martin ; Trnka, Tomáš (referee) ; Veselý, Jan (advisor)
With regard to a fast development in the field of fluoroorganic chemisty, the intention of this diploma thesis is focused to utilize of organocatalysis by secondary amines as catalysts for preparation enantiomerically pure compounds containing fluorine atom in its structure. The preparation of these subsances is realized by way of nucleofilic addition to α,β- unsaturated aldehydes using suitable fluorine containing nuclephilic agent 1-(fluoronitromethylsulphonyl)benzene, to get appropriate 1,4-adduct.
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|
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Enantioselective synthesis of fluorinated organic compounds using iminium and enamine catalysis
Hejnová, Monika ; Veselý, Jan (advisor) ; Smrček, Stanislav (referee)
This diploma thesis deals with the scope of organocatalytic concept for the preparation of enantiomerically pure organic compounds, containing fluorine atom. Our attention was focused on the use of easily available α,β-unsaturated aldehydes and ketones as starting materials and commercially available secondary amines as catalysts. The first part of the work is dedicated to the enantioselective cyclization reaction of hydrazone (24) with cyclohex-2-enone (25). The second part describes a study of enantioselective nucleophilic addition of diethyl 2-fluoromalonate (31a) to α,β-unsaturated aldehydes (30) via enamine activation.
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