Journal
CHIRALITY
Volume 33, Issue 1, Pages 22-36Publisher
WILEY
DOI: 10.1002/chir.23283
Keywords
1,2-diamines; aldol reaction; asymmetric organocatalysis; bifunctional prolinamides; C-2-symmetry axis; stereoselectivity; wet solvent-free
Funding
- Consejo Nacional de Ciencia y Tecnologia (CONACYT) [286620, 170296, 290754]
- Laboratorio Nacional de Supercomputo del Sureste de Mexico
- Consejo Nacional de Ciencia y Tecnologia (CONACYT) network of national laboratories
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This study synthesized novel organic compounds, and successfully carried out highly enantioselective and diastereoselective reactions using organocatalysts under solvent-free conditions in the presence of water, achieving effective stereoselective induction.
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.
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