Hybrid Peptide–Thiourea Catalyst for Asymmetric Michael Additions of Aldehydes to Heterocyclic Nitroalkenes
- Patrícia ČmelováPatrícia ČmelováDepartment of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, SlovakiaMore by Patrícia Čmelová
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- Denisa VargováDenisa VargováDepartment of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, SlovakiaMore by Denisa Vargová
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- Radovan Šebesta*Radovan Šebesta*Email: [email protected]Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, SlovakiaMore by Radovan Šebesta
Abstract
Bifunctional organocatalysis combining covalent and noncovalent activation is presented. The hybrid peptide–thiourea catalyst features a N-terminal proline moiety for aldehyde activation and a thiourea unit for electrophile activation. This catalyst effectively promotes asymmetric Michael additions of aldehydes to challenging but biologically relevant heterocycle-containing nitroalkenes. The catalyst can be used under solvent-free conditions. Spectroscopic and density functional theory studies elucidate the catalyst structure and mode of action.
Cited By
This article is cited by 7 publications.
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