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Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies
Third-party funded project |
Project title |
Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies |
Principal Investigator(s) |
Sparr, Christof
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Organisation / Research unit |
Departement Chemie / Organische Chemie (Sparr) |
Project start |
01.10.2014 |
Probable end |
30.09.2017 |
Status |
Completed |
Abstract |
The configuration of axially chiral compounds fully governs the biological activity of important pharmaceutical entities and is completely translated from atropisomeric ligands to high-value products in numerous remarkably efficient catalytic processes. However, atroposelective catalysis remained a niche area in the vast field of asymmetric synthesis. This underrepresentation offers intriguing opportunities for the development of novel synthetic methods and strategies. Inspired by the aromatic polyketide biosynthesis, the proposed method takes advantage of an aromatization as ample driving force and utilizes efficient transfer of central to axial chirality from the catalyst to the product. Readily available substrates will be treated with secondary amine organocatalysts to initiate a cyclization event, inducing an aromatization process to selectively form the desired atropisomer after release of the catalyst. |
Keywords |
catalysis, rapid generation of molecular complexity, environmentally benign chemistry, reaction cascades, reaction mechanisms |
Financed by |
Swiss National Science Foundation (SNSF)
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Published results () |
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ID |
Autor(en) |
Titel |
ISSN / ISBN |
Erschienen in |
Art der Publikation |
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3347455 |
Link, Achim; Fischer, Christian; Sparr, Christof |
Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents |
1433-7851 ; 1521-3773 |
Angewandte Chemie International Edition |
Publication: JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
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3698771 |
Fäseke, Vincent C.; Sparr, Christof |
Stereoselective Arene-Forming Aldol Condensation: Synthesis of Axially Chiral Aromatic Amides |
1433-7851 ; 1521-3773 |
Angewandte Chemie International Edition |
Publication: JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
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4190021 |
Link, Achim; Fischer, Christian; Sparr, Christof |
A 1,5-Bifunctional Organomagnesium Reagent for the Synthesis of Disubstituted Anthracenes and Anthrones |
0039-7881 ; 1437-210X |
Synthesis |
Publication: JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
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4190039 |
Fäseke, Vincent C.; Witzig, Reto M.; Link, Achim; Lotter, Dominik; Sparr, Christof |
Catalytic Arene-forming Aldol Condensation: Stereoselective Synthesis of Rotationally Restricted Aromatic Compounds |
0009-4293 |
Chimia |
Publication: JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
|
4190046 |
Witzig, Reto M.; Lotter, Dominik; Fäseke, Vincent C.; Sparr, Christof |
Stereoselective Arene-Forming Aldol Condensation: Catalyst-Controlled Synthesis of Axially Chiral Compounds |
0947-6539 ; 1521-3765 |
Chemistry - A European Journal |
Publication: JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift) |
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24/04/2024
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