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- Title
Supramolecular Catalysis with Chiral Mono- and Bis-(Thio)Urea-Derivatives.
- Authors
Iuliano, Veronica; Della Sala, Paolo; Talotta, Carmen; De Rosa, Margherita; Gaeta, Carmine; Neri, Placido; Soriente, Annunziata
- Abstract
Chiral mono- and bis-(thio)urea supramolecular organocatalysts were studied in the enantioselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF) to carbonylic compounds; the corresponding chiral γ-hydroxymethyl-butenolides are obtained in good yields and with high enantiomeric excesses. The catalyst structure, as well as the reaction conditions, strongly influence the efficiency of the reaction. The conformational features of mono(thio)urea catalysts 2 and 3 and bis(thio)urea catalysts 7 and 8 were investigated by DFT calculations along with the structure of their complexes with benzaldehyde. Natural Bond Orbital (NBO) and Non-Covalent Interaction (NCI) calculations provided useful information concerning the activating H-bonding interactions in the complexes.
- Subjects
CATALYSIS; UREA derivatives; CHIRALITY; ADDITION reactions; FURANS
- Publication
Organics, 2024, Vol 5, Issue 2, p32
- ISSN
2673-401X
- Publication type
Article
- DOI
10.3390/org5020003