Affiliation:
1. Department of Organic Chemistry and Technology Budapest University of Technology and Economics Műegyetem rkp. 3 1111 Budapest Hungary
2. Euroapi Hungary Kft. Tó utca 1–5 1045 Budapest Hungary
3. ELKH-BME Computation Driven Chemistry Research Group Department of Inorganic and Analytical Chemistry Budapest University of Technology and Economics Műegyetem rkp. 3 1111 Budapest Hungary
4. Furukawa Electric Institute of Technology Késmárk utca 28/A 1157 Budapest Hungary
5. Department of Pharmacognosy Semmelweis University Üllői út. 26 1085 Budapes Hungary
Abstract
AbstractIn this study, we describe the synthesis of cinchona (thio)squaramide and a novel cinchona thiourea organocatalyst. These catalysts were employed in pharmaceutically relevant catalytic asymmetric reactions, such as Michael, Friedel–Crafts, and A3 coupling reactions, in combination with Ag(I), Cu(II), and Ni(II) salts. We identified several organocatalyst‐metal salt combinations that led to a significant increase in both yield and enantioselectivity. To gain insight into the active catalyst species, we prepared organocatalyst‐metal complexes and characterized them using HRMS, NMR spectroscopy, and quantum chemical calculations (B3LYP‐D4/def2‐TZVP), which allowed us to establish a structure‐activity relationship.
Funder
Budapesti Műszaki és Gazdaságtudományi Egyetem
European Commission