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- Title
Diastereoselective Nitroaldol Reaction Catalyzed by Binuclear Copper(II) Complexes in Aqueous Medium.
- Authors
Arunachalam, Rajendran; Aswathi, Chirayil S.; Das, Anjan; Kureshy, Rukhsana I.; Subramanian, Palani S.
- Abstract
Polydentate ligands 1 and 2, which incorporate a terminal pyridyl moiety and an oxygen-rich oxalate dihydrizide/malonic dihydrizide spacer moiety, as well as their binuclear metal complexes [Cu212] and [Cu222], which adopt a 1:1 metal/ligand ratio, were synthesized and characterized. Both complexes were screened for their catalytic activity in the nitroaldol reaction, in which [Cu212] worked efficiently as catalyst for both substituted benzaldehyde and pyridinecarboxaldehyde, whereas [Cu222] is highly substrate specific and showed activity towards nitro-substituted aldehydes and pyridinecarboxaldehyde. Furthermore, as helicates are intrinsically chiral, the stereochemical architecture in the binuclear double-stranded Cu2 helicates as catalyst favored the diastereoselective syn product with nitroethane and nitropropane and their respective diastereoselectivities were determined by using ¹H NMR spectroscopy.
- Subjects
COPPER compounds; LIGANDS (Chemistry); ENANTIOSELECTIVE catalysis; NITROETHANE; NITROPROPANE; NUCLEAR magnetic resonance spectroscopy
- Publication
ChemPlusChem, 2015, Vol 80, Issue 1, p209
- ISSN
2192-6506
- Publication type
Article
- DOI
10.1002/cplu.201402200