Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies

Research Project
|
01.10.2014
- 30.09.2017

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.

Funding

Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies

SNF Projekt (GrantsTool), 04.2014-03.2017 (36)

PI : Sparr, Christof.

Publications

Fäseke, Vincent C. et al. (2017) ‘Catalytic Arene-forming Aldol Condensation: Stereoselective Synthesis of Rotationally Restricted Aromatic Compounds’, Chimia, 71(9), pp. 596–599. Available at: https://doi.org/10.2533/chimia.2017.596.

URLs

Link, Achim, Fischer, Christian and Sparr, Christof (2017) ‘A 1,5-Bifunctional Organomagnesium Reagent for the Synthesis of Disubstituted Anthracenes and Anthrones’, Synthesis, 49(2), pp. 397–402. Available at: https://doi.org/10.1055/s-0036-1588087.

URLs

Witzig, Reto M. et al. (2017) ‘Stereoselective Arene-Forming Aldol Condensation: Catalyst-Controlled Synthesis of Axially Chiral Compounds’, Chemistry - A European Journal, 23(53), pp. 12960–12966. Available at: https://doi.org/10.1002/chem.201702471.

URLs

Fäseke, Vincent C. and Sparr, Christof (2016) ‘Stereoselective Arene-Forming Aldol Condensation: Synthesis of Axially Chiral Aromatic Amides’, Angewandte Chemie International Edition, 55(25), pp. 7261–4. Available at: https://doi.org/10.1002/anie.201602689.

URLs

Link, Achim, Fischer, Christian and Sparr, Christof (2015) ‘Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents’, Angewandte Chemie International Edition, 54(41), pp. 12163–12166. Available at: https://doi.org/10.1002/anie.201505414.

URLs

Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies

Research Project
|
01.10.2014
- 30.09.2017

Funding

Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies

SNF Projekt (GrantsTool), 04.2014-03.2017 (36)

PI : Sparr, Christof.

Publications

Fäseke, Vincent C. et al. (2017) ‘Catalytic Arene-forming Aldol Condensation: Stereoselective Synthesis of Rotationally Restricted Aromatic Compounds’, Chimia, 71(9), pp. 596–599. Available at: https://doi.org/10.2533/chimia.2017.596.

Link, Achim, Fischer, Christian and Sparr, Christof (2017) ‘A 1,5-Bifunctional Organomagnesium Reagent for the Synthesis of Disubstituted Anthracenes and Anthrones’, Synthesis, 49(2), pp. 397–402. Available at: https://doi.org/10.1055/s-0036-1588087.

Witzig, Reto M. et al. (2017) ‘Stereoselective Arene-Forming Aldol Condensation: Catalyst-Controlled Synthesis of Axially Chiral Compounds’, Chemistry - A European Journal, 23(53), pp. 12960–12966. Available at: https://doi.org/10.1002/chem.201702471.

Fäseke, Vincent C. and Sparr, Christof (2016) ‘Stereoselective Arene-Forming Aldol Condensation: Synthesis of Axially Chiral Aromatic Amides’, Angewandte Chemie International Edition, 55(25), pp. 7261–4. Available at: https://doi.org/10.1002/anie.201602689.

Link, Achim, Fischer, Christian and Sparr, Christof (2015) ‘Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents’, Angewandte Chemie International Edition, 54(41), pp. 12163–12166. Available at: https://doi.org/10.1002/anie.201505414.

Members (1)

Christof Sparr

Principal Investigator

Research Groups

Synthetic Methods and Stereoselective Catalysis

Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies

Research Project | 01.10.2014 - 30.09.2017

Funding

Atropselective Secondary Amine Catalysis: Method Development and Mechanistic Studies

SNF Projekt (GrantsTool), 04.2014-03.2017 (36)

PI : Sparr, Christof.

Publications

Fäseke, Vincent C. et al. (2017) ‘Catalytic Arene-forming Aldol Condensation: Stereoselective Synthesis of Rotationally Restricted Aromatic Compounds’, Chimia, 71(9), pp. 596–599. Available at: https://doi.org/10.2533/chimia.2017.596.

Link, Achim, Fischer, Christian and Sparr, Christof (2017) ‘A 1,5-Bifunctional Organomagnesium Reagent for the Synthesis of Disubstituted Anthracenes and Anthrones’, Synthesis, 49(2), pp. 397–402. Available at: https://doi.org/10.1055/s-0036-1588087.

Witzig, Reto M. et al. (2017) ‘Stereoselective Arene-Forming Aldol Condensation: Catalyst-Controlled Synthesis of Axially Chiral Compounds’, Chemistry - A European Journal, 23(53), pp. 12960–12966. Available at: https://doi.org/10.1002/chem.201702471.

Fäseke, Vincent C. and Sparr, Christof (2016) ‘Stereoselective Arene-Forming Aldol Condensation: Synthesis of Axially Chiral Aromatic Amides’, Angewandte Chemie International Edition, 55(25), pp. 7261–4. Available at: https://doi.org/10.1002/anie.201602689.

Link, Achim, Fischer, Christian and Sparr, Christof (2015) ‘Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organo­magnesium Reagents’, Angewandte Chemie International Edition, 54(41), pp. 12163–12166. Available at: https://doi.org/10.1002/anie.201505414.

Members (1)

Christof Sparr

Principal Investigator

Research Groups

Synthetic Methods and Stereoselective Catalysis

Research Project
|
01.10.2014
- 30.09.2017

Link, Achim, Fischer, Christian and Sparr, Christof (2015) ‘Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents’, Angewandte Chemie International Edition, 54(41), pp. 12163–12166. Available at: https://doi.org/10.1002/anie.201505414.