thiourea has been researched along with prolinamide* in 2 studies
2 other study(ies) available for thiourea and prolinamide
| Article | Year |
|---|---|
Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions.
In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1-4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene ent-8. Highly enantioselective and diastereoselective aldolic intermolecular reactions (up to 95% enantiomeric excess, 93:7 anti/syn) between aliphatic ketones (20 equiv) and a range of aromatic aldehydes (1 equiv) were successfully carried out in the presence of water (10 equiv) and monochloroacetic acid (10 mol%), solvent-free conditions, at room temperature over 24 h using organocatalysts 1-7 (5 mol%). Stereoselective induction using density functional theory-based methods was consistent with the experimental data. Topics: Acetone; Aldehydes; Catalysis; Chemistry Techniques, Synthetic; Density Functional Theory; Ketones; Molecular Structure; Proline; Solvents; Stereoisomerism; Thiourea | 2021 |
A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst.
A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99:1 dr and 99% ee). Both the chiral centers of the diamine unit are essential, while the thiourea hydrogen originating from the amine and the amide hydrogen play a predominant role for the catalyst efficiency. Topics: Aldehydes; Catalysis; Ethylenediamines; Hydrogen; Isomerism; Ketones; Oligopeptides; Proline; Stereoisomerism; Thiourea | 2012 |