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Hybrid Peptide–Thiourea Catalyst for Asymmetric Michael Additions of Aldehydes to Heterocyclic Nitroalkenes

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journal contribution
posted on 01.12.2020, 13:40 authored by Patrícia Čmelová, Denisa Vargová, Radovan Šebesta
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.