Stereoselective, Catalytic Annulation Methods to Create Structurally Well-Defined Scaffolds
Research Project
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01.11.2015
- 31.10.2020
UNIverse - Public Research Portal
Structurally well-defined objects are the elements required for the rational design of molecular backbones. The development of novel synthetic methods for the formation of new aromatic rings will provide unique scaffolds, which are not readily accessible otherwise. The catalyst controlled stereoselective arene-forming aldol condensation to form compounds with axial, helical or planar chirality will be investigated in detail. In the examined cascade reactions, the stereochemical information of small amine catalysts is transferred into new chirality elements leading to different, structurally distinct molecular architectures. The well-defined scaffolds will subsequently be employed to position various groups into a predictable spatial arrangement with respect to each other.
Funding
Stereoselective, Catalytic Annulation Methods to Create Structurally Well-Defined Scaffolds
SNF Projekt (GrantsTool), 02.2015-01.2020 (60)
PI : Sparr, Christof.
Publications
Schmidt, Tanno A. and Sparr, Christof (2021) ‘Catalyst Control over Twofold and Higher-Order Stereogenicity by Atroposelective Arene Formation’, Accounts of Chemical Research, 54(12), pp. 2764–2774. Available at: https://doi.org/10.1021/acs.accounts.1c00178.
Schmidt, Tanno A. and Sparr, Christof (2021) ‘Catalyst-Controlled Stereoselective Barton-Kellogg Olefination’, Angewandte Chemie International Edition, 60(44), pp. 23911–23916. Available at: https://doi.org/10.1002/anie.202109519.
Triandafillidi, Ierasia et al. (2021) ‘Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide’, Chemical Science, 12(30), pp. 10191–10196. Available at: https://doi.org/10.1039/d1sc02360h.
Wu, Xingxing et al. (2021) ‘Catalyst control over sixfold stereogenicity’, Nature Catalysis, 4(6), pp. 457–462. Available at: https://doi.org/10.1038/s41929-021-00615-z.
Castrogiovanni, Alessandro et al. (2020) ‘JoyaPhos: An Atropisomeric Teraryl Monophosphine Ligand’, Chemistry - A European Journal, 26(44), pp. 9864–9868. Available at: https://doi.org/10.1002/chem.202001269.
Moser, Daniel et al. (2020) ‘Catalytic Cascade Reactions Inspired by Polyketide Biosynthesis’, Chimia, 74(9), pp. 699–703. Available at: https://doi.org/10.2533/chimia.2020.699.
Raps, Felix C. et al. (2020) ‘Catalyst-Controlled Transannular Polyketide Cyclization Cascades: Selective Folding of Macrocyclic Polyketides’, Angewandte Chemie International Edition, 59(42), pp. 18390–18394. Available at: https://doi.org/10.1002/anie.202005733.
Witzig, Reto M. and Sparr, Christof (2020) ‘Synthesis of Enantioenriched Tetra-ortho-3,3′-substituted Biaryls by Small-Molecule-Catalyzed Noncanonical Polyketide Cyclizations’, Synlett, 31(1), pp. 13–20. Available at: https://doi.org/10.1055/s-0039-1690215.
Wu, Xingxing et al. (2020) ‘Catalyst-Control over Sixfold Stereogenicity’, ChemRxiv [Preprint]. Cambridge University Press. Available at: https://doi.org/10.26434/chemrxiv.12213362.v1.
Zilate, Bouthayna, Fischer, Christian and Sparr, Christof (2020) ‘Design and application of aminoacridinium organophotoredox catalysts’, Chemical Communications, 56(12), pp. 1767–1775. Available at: https://doi.org/10.1039/c9cc08524f.
Castrogiovanni, Alessandro et al. (2019) ‘Shortcuts for Electron-Transfer through the Secondary Structure of Helical Oligo-1,2-Naphthylenes’, Chemistry - A European Journal, 25, pp. 16748–16754. Available at: https://doi.org/10.1002/chem.201904771.
Witzig, Reto M. et al. (2019) ‘Atroposelective synthesis of tetra-ortho-substituted biaryls by catalyst-controlled non-canonical polyketide cyclizations’, Nature Catalysis, 2(10), pp. 925–930. Available at: https://doi.org/10.1038/s41929-019-0345-0.
Fischer, Christian and Sparr, Christof (2018) ‘Configurationally Stable Atropisomeric Acridinium Fluorophores’, Synlett, 29(16), pp. 2176–2180. Available at: https://doi.org/10.1055/s-0037-1610233.
Fischer, Christian and Sparr, Christof (2018) ‘Synthesis of 1,5-Bifunctional Organolithium Reagents by Double Directed ortho-Metalation: Direct Transformation of Esters into 1,8-Dimethoxy-Acridinium Salts’, Tetrahedron, 74(38), pp. 5486–5493. Available at: https://doi.org/10.1016/j.tet.2018.04.060.
Link, Achim and Sparr, Christof (2018) ‘Stereoselective Arene-Formation (Review)’, Chemical Society Reviews, 47(11), pp. 3804–3815. Available at: https://doi.org/10.1039/c7cs00875a.
Link, Achim and Sparr, Christof (2018) ‘Remote Central-to-Axial Chirality Conversion: Direct Atroposelective Ester to Biaryl Transformation’, Angewandte Chemie International Edition, 57(24), pp. 7136–7139. Available at: https://doi.org/10.1002/anie.201803472.
Lotter, Dominik et al. (2018) ‘Catalyst-Controlled Stereodivergent Synthesis of Atropisomeric Multi-Axis Systems’, ACS Central Science, 4(5), pp. 656–660. Available at: https://doi.org/10.1021/acscentsci.8b00204.
Lotter, Dominik and Sparr, Christof (2018) ‘Diaryl Magnesium Lithium Alkoxides Derived from (Z)‐4‐(2‐Bromophenyl)but‐3‐en‐1‐ol’, Encyclopedia of Reagents for Organic Synthesis [Preprint]. Available at: https://doi.org/10.1002/047084289x.rn02170.
Zilate, Bouthayna, Castrogiovanni, Alessandro and Sparr, Christof (2018) ‘Catalyst-Controlled Stereoselective Synthesis of Atropisomers (Perspective)’, ACS Catalysis, 8(4), pp. 2981–2988. Available at: https://doi.org/10.1021/acscatal.7b04337.
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.
Lotter, Dominik et al. (2016) ‘Stereoselective Arene-Forming Aldol Condensation: Synthesis of Configurationally Stable Oligo-1,2-naphthylenes’, Angewandte Chemie International Edition, 55(8), pp. 2920–2923. Available at: https://doi.org/10.1002/anie.201510259.
Members (1)
Christof Sparr
Principal Investigator
Research Groups