Novel Selenoureas Based on Cinchona Alkaloid Skeleton: Synthesis and Catalytic Investigations

Mariola Zielińska-Błajet; Joanna Najdek

doi:10.3390/ma14030600

Novel Selenoureas Based on Cinchona Alkaloid Skeleton: Synthesis and Catalytic Investigations

Materials (Basel). 2021 Jan 28;14(3):600. doi: 10.3390/ma14030600.

Authors

Mariola Zielińska-Błajet¹, Joanna Najdek²

Affiliations

¹ Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
² Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.

Abstract

An efficient approach to the synthesis of chiral selenoureas consisting of Cinchona alkaloid scaffolds was described. The new selenoureas were assessed as bifunctional organocatalysts in the asymmetric Michael addition reactions under mild conditions. The best results were obtained for selenoureas bearing the 4-fluorophenyl group. These catalysts promoted the reactions with enantioselectivities of up to 96% ee. Additionally, the catalytic performance of the thiourea and selenourea counterpart was compared.

Keywords: Cinchona alkaloids; Michael addition; asymmetric synthesis; isoselenocyanates; organocatalysis; selenoureas.