About the Cocatalysis Research Group
Welcome to the forefront of transformative research in the realm of cocatalysis!
Our vision
Our research group is dedicated to pushing the boundaries of chemical reactivity, with a profound commitment to environmental stewardship and sustainability. The central challenge we address is the development of environmentally benign methods for synthesizing complex compounds, particularly those that are chiral. Our focus is on leveraging asymmetric organocatalysis, a field that employs renewable and less toxic small organic molecules as catalysts, in lieu of traditional transition metals. Asymmetric organocatalysis and particularly cocatalysis, with its adherence to green chemistry principles, emerges as a beacon of future technology, promising advancements that prioritize safety, efficiency, and minimal environmental impact. In an era where the demand for new chemicals, particularly in the pharmaceutical industry, is ever-growing, we strive to reduce waste, energy consumption, and environmental impact. By harnessing the synergistic effects of different catalytic systems, we want to develop innovative processes that meet societal needs and align with the goals of sustainable chemistry.
Our current project
The cocatalysis group was founded in 2024. Our first project aims to implement classical organocatalytic approaches with borane catalysis, thereby unlocking novel reactivity that can revolutionize the synthesis of chiral amino alcohols and diamines. These motifs are widely represented in the structure of bioactive molecules and hold immense potential for applications in pharmaceuticals and beyond. As direct access to these motifs in an enantioselective manner is rare, a strategy enabling their synthesis in an atom-efficient approach would be highly valuable to the chemical community.
For students!
Feel free to join us as we redefine the landscape of chemical synthesis, contributing to a sustainable future where scientific innovation and environmental consciousness go hand in hand.
Group Members
Publications
Kaasik, M.; Kanger, T. Halogen‐Bonding Organocatalysis – New Opportunities for Asymmetric Synthesis. In: L. Albrecht, A. Albrecht, L. Dell'Amico (Ed.). Asymmetric Organocatalysis. New Strategies, Catalysts, and Oppurtunities. 2022, chapter 6, 203−224. Wiley VCH. https://doi.org/10.1002/9783527832217.ch6
Published prior to establishing the cocatalysis group:
11. Casper Larsen Barløse, C. L.; Faghtmann, J.; Kaasik, M.; Mastroddi, R.; Jørgensen, K. A. Exploring Heterotropones and Examining Their Propensity to Undergo [4 + 2] Cycloadditions. Organic Letters, 2024, 26(8), 1539–1543. https://doi.org/10.1021/acs.orglett.3c04080
10. Kaasik, M.; Chen, P.-P.; Ričko, S.; Jørgensen, K. A.; Houk, K. N. Asymmetric [4 + 2], [6 + 2], and [6 + 4] Cycloadditions of Isomeric Formyl Cycloheptatrienes Catalyzed by a Chiral Diamine Catalyst. Journal of the American Chemical Society, 2023, 145, 23874−23890. https://doi.org/10.1021/jacs.3c09551
9. Ričko, S.; Bitsch, R. S.; Kaasik, M.; Otevřel, J.; Højgaard Madsen, M.; Keimer, A.; Jørgensen, K. A. Enantioconvergent 6π Electrocyclization Enabled by Photoredox Racemization. Journal of the American Chemical Society 2023, 145, 20913−20926. https://doi.org/10.1021/jacs.3c06227
8. Kriis, K.; Martõnov, H.; Miller, A.; Erkman, K.; Järving, I.; Kaasik, M.; Kanger, T. Multifunctional Catalysts in the Asymmetric Mannich Reaction of Malononitrile with N-Phosphinoylimines: Coactivation by Halogen Bonding versus Hydrogen Bonding. Journal of Organic Chemistry 2022, 87 (11), 7422−7435. https://doi.org/10.1021/acs.joc.2c00674
7. Kaasik, M.; Martõnova, J.; Erkman, K,: Metsala, A.; Järving, I.; Kanger, T. Enantioselective Michael addition to vinyl phosphonates via hydrogen bond-enhanced halogen bond catalysis. Chemical Science 2021, 12, 7561-7568. https://doi.org/10.1039/D1SC01029H
6. Kaasik, M.; Kanger, T. Supramolecular Halogen Bonds in Asymmetric Catalysis. Frontiers in Chemistry 2020, 8, 599064. https://doi.org/10.3389/fchem.2020.599064
5. Kaasik, M.; Metsala, A.; Kaabel, S.; Kriis, K.; Järving, I.; Kanger, T. Halo-1,2,3-triazolium Salts as Halogen Bond Donors for the Activation of Imines in Dihydropyridinone Synthesis. Journal of Organic Chemistry 2019, 84, 4294−4303. https://doi.org/10.1021/acs.joc.9b00248
4. Kaasik, M.; Kaabel, S.; Kriis, K.; Järving, I.; Kanger, T. Synthesis of Chiral Triazole-Based Halogen Bond Donors. Synthesis 2019, 51, 2128-2135. https://doi.org/10.1055/s-0037-1610864
3. Peterson, A.; Kaasik, M.; Metsala, A.; Järving, I.; Adamson, J.; Kanger, T. Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors. RSC Advances 2019, 9, 11718−11721. https://doi.org/10.1039/C9RA01692A
2. Kaasik, M.; Kaabel, S.; Kriis, K.; Järving, I.; Aav, R.; Rissanen, K.; Kanger, T. Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution. Chemistry - A European Journal 2017, 23, 7337−7344. https://doi.org/10.1002/chem.201700618
1. Kaasik, M.; Noole, A.; Reitel, K.; Järving, I.; Kanger, T. Organocatalytic Conjugate Addition of Cyclopropylacetaldehyde Derivatives to Nitro Olefins: en Route to β- and γ-Amino Acids. European Journal of Organic Chemistry 2015, 8, 1745−1753. https://doi.org/10.1002/ejoc.201403387
Projects
- PSG951 "Merging Organocatalysis with Borane Catalysis in Asymmetric Synthesis (01.01.2024–31.12.2028)", Mikk Kaasik, Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology
- STP48 "A novel cocatalytic approach for asymmetric synthesis (01.12.2023–01.01.2024)", Mikk Kaasik, Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology
- PUTJD1021 "Expanding the borders of higher-order cycloadditions (01.05.2021–30.04.2023)", Mikk Kaasik, Tallinn University of Technology, School of Science, Department of Chemistry and Biotechnology
Open Positions
- We are looking for an enthusiastic PhD student, who can help us with our current project. Applications will be possible until the position is filled. For more information click HERE!
- Students who would like to realize themselves in the laboratory in the field of organic synthetic chemistry and explore various catalytic approaches, feel free to contact us.
News
The Cocatalysis Research Group is gaining momentum!
The positive funding decision from ETAG and the allocation of startup grant PSG951 mean that over the next 5 years, it will be possible to lay a strong foundation, upon which to build an innovative and diverse research group!
Our Group In and Out of Lab
Mikk enjoys playing board games, occasionally joined by Aleksandra. She really likes different types of handicraft. They both share the view that rock music is the ideal first choice.
