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Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as Organocatalysts
- Source :
- RUA. Repositorio Institucional de la Universidad de Alicante, Universidad de Alicante (UA)
- Publication Year :
- 2013
- Publisher :
- American Chemical Society (ACS), 2013.
-
Abstract
- Wet unsupported and supported 1,1′-binaphthalene-2,2′-diamine (BINAM) derived prolinamides are efficient organocatalysts under solvent-free conditions at room temperature to perform the synthesis of chiral tacrine analogues in good yields (up to 93%) and excellent enantioselectivies (up to 96%). The Friedländer reaction involved in this process takes place with several cyclohexanone derivatives and 2-aminoaromatic aldehydes, and it is compatible with the presence of either electron-withdrawing or electron-donating groups at the aromatic ring of the 2-aminoaryl aldehyde derivatives used as electrophiles. The reaction can be extended to cyclopentanone derivatives, affording a regioisomeric but separable mixture of products. The use of the wet silica gel supported organocatalyst, under solvent-free conditions, for this process led to the expected product (up to 87% enantiomeric excess), with its reuse being possible at least up to five times. This work was financially supported by the Ministerio de Ciencia e Innovación (MICINN: Projects: CTQ2010-20387 and Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (Prometeo/2009/039, the University of Alicante and the EU (ORCA action CM0905). A.B.-C. thanks the Spanish MICINN for a predoctoral fellowship (FPU AP2009-3601).
- Subjects :
- Proline
Cyclohexanone
Diamines
Naphthalenes
Cyclopentanone
Aldehyde
Catalysis
chemistry.chemical_compound
Diamine
Organic chemistry
Enantiomeric excess
Friedländer condensation
Enantioselective
chemistry.chemical_classification
Solvent-free
Molecular Structure
Organocatalysis
Chemistry
Organic Chemistry
Enantioselective synthesis
Stereoisomerism
Química Orgánica
Electrophile
Tacrine
Wet 1,1′-binaphthalene-2,2′-diamine-derived prolinamides
Subjects
Details
- ISSN :
- 15206904, 00223263, and 20102038
- Volume :
- 78
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....4edbdca4597a351c3fc264e683ad813d